Silicone adhesive composition and an adhesive tape

ABSTRACT

One of the purposes of the present invention is to provide a silicone adhesive composition which provides an adhesive layer having an excellent antistatic property and which has an excellent strength of bond to a tape substrate and, therefore, when an adhesive tape or film having the adhesive layer is peeled from a tape-stuck body, less residual adhesive occurs on the tape-stuck body. The other purpose of the present invention is to provide a silicone adhesive composition which cures well by heating for a short time, particularly for less than 5 minutes, to provide an adhesive layer having an excellent antistatic property. The present invention first provides a silicone adhesive composition comprising (A) an addition reaction-curable silicone, (B1) a compound having at least two unsaturated hydrocarbon groups and two (poly)oxyalkylene residues in one molecule, and (C) an ionic liquid containing no lithium. The present invention secondly provides a silicone adhesive composition comprising (A) an addition reaction-curable silicone, (B) a compound having at least one unsaturated hydrocarbon group and at least one (poly)oxyalkylene residue in one molecule, (C) an ionic liquid containing no lithium and (e) a platinum group metal catalyst which is not a complex with a compound having an unsaturated hydrocarbon bond.

This application is a national stage application under 35 USC 371 ofinternational application PCT/JP2016/062661 filed Apr. 21, 2016, whichclaims priority from Japan application 2015-091528 filed Apr. 28, 2015and from Japan application 2015-091473 filed Apr. 28, 2015, the entirecontents of which are hereby incorporated herein by reference.

FIELD OF THE INVENTION

The present invention relates to a silicone adhesive composition and anadhesive tape. More particularly, the present invention relates to asilicone adhesive composition having an excellent antistatic propertyand to an adhesive tape comprising the composition.

BACKGROUND OF THE INVENTION

Recently, electronic equipments have become thinner, lighter andsmaller. Accordingly, electronic parts to be mounted in the electronicequipments have also become smaller. Silicone adhesive tapes have beenwidely used as an adhesive tape in processing because of their high heatresistance and as an adhesive tape in transfer because of their goodpeelability.

However, silicone adhesives are electrically highly insulating and,therefore, may cause peeling electrification and, at worst, may cause adielectric breakdown of the electronic part when a thin and smallelectronic part is peeled. In order to prevent the peelingelectrification, it is needed to develop an antistatic siliconeadhesive.

For example, Patent Literatures 1 and 2 describe antistatic adhesivetapes whose tape substrates are antistatic. Such adhesive tapes haveproblems that tape substrates to be used are limited, and peelingelectrification is not prevented in a case where the adhesive iselectrically insulating. Patent Literatures 3, 4 and 5 describeantistatic adhesive tapes having an antistatic layer between an adhesivelayer and a tape substrate. The use of an adhesive tape worsensproductivity due to steps of the production of the adhesive tape.Further, peeling electrification is not prevented in a case where theadhesive is electrically insulating, as described for the aforesaidantistatic adhesive tape.

Patent Literatures 6, 7, 8 and 9 describe antistatic adhesive tapeswhose adhesives are antistatic. Patent Literature 6 describes that theadhesive comprises carbon black. Patent Literature 7 describes that theadhesive comprises a polyol. Patent Literatures 8 and 9 describe thatthe adhesive comprises electrically conductive microparticles dispersedtherein.

A polyether polyol is less compatible with a silicone adhesive.Therefore, the adhesive comprising the polyol may be cloudy and causeseparation of the polyol with time. The compound needs to be added in alarge amount and, therefore, the adhesive comprising the compound maynot have a desired adhesion strength. Further, in a case where thisadhesive is used to form an adhesive tape, a strength of bond betweenthe adhesive and a tape substrate is lower, so that the adhesive mayremain on a tape-stuck body when the adhesive tape is peeled from thetape-stuck body. The adhesive comprising carbon black has suchdisadvantages that washing of an apparatus for producing an adhesivetape is a troublesome work due to carbon black; the adhesive tape has anopaque, black appearance and an unstable surface resistivity; and carbonremains on a tape-stuck body such as an electronic element after theadhesive tape is peeled from the tape-stuck body. Further, the adhesivecomprising electrically conductive microparticles is opaque, and may notattain a desired performance due to separation of the electricallyconductive microparticles caused by a difference in specific gravitiesbetween the adhesive composition and the electrically conductivemicroparticles.

Patent Literature 10 describes a silicone adhesive compositioncomprising an ion conductive antistatic agent which is a lithium salt,and that a silicone adhesive tape comprising the adhesive compositionhas an excellent antistatic property and maintains the antistaticproperty even after exposed to a high temperature for a long time. ThisLiterature also describes that the antistatic property is improved byadding the ion conductive antistatic agent in such a manner that theagent is dissolved in an organic solvent having an oxyalkylene group.Patent Literature 10 refers to the following compounds as the organicsolvent having an oxyalkylene group:R³—(C═O)—O—(R⁴—O)_(m)—R⁵wherein R³ is an alkyl group having 1 to 12 carbon atoms, R⁴ may beidentical to or different from each other and are each a polymethylenegroup having 2 to 8 carbon atoms, R⁵ is a hydrogen atom or an alkylgroup having 1 to 12 carbon atoms, and m is an integer of 2 to 50, andR⁶—(O—R⁷)_(n)—O—(C═O)—R⁸—(C═O)—O—(R⁷—O)_(p)—R⁶wherein R⁶ may be identical to or different from each other and are eacha hydrogen atom or an alkyl group having 1 to 12 carbon atoms, R⁷ and R⁸may be identical to or different from each other and are each anethylene group or a polymethylene group having 3 to 12 carbon atoms, andn and p may be identical to or different from each other and are each aninteger of 2 to 50.

PRIOR LITERATURES Patent Literatures

Patent Literature 1: JP application Laid-Open Hei 4-216887/1992

Patent Literature 2: JP Application Laid-Open 2003-306654

Patent Literature 3: JP Application Laid-Open Sho 63-380/1988

Patent Literature 4: JP Application Laid-Open Hei 4-135791/1992

Patent Literature 5: JP Application Laid-Open Hei 6-220408/1994

Patent Literature 6: JP Application Laid-Open Sho 61-136573/1986

Patent Literature 7: JP Application Laid-Open 2005-154491

Patent Literature 8: JP Application Laid-Open 2004-091703

Patent Literature 9: JP Application Laid-Open 2004-091750

Patent Literature 10: Japanese Patent No. 5309714

SUMMARY OF THE INVENTION Problems to be Solved by the Invention

The oxyalkylene solvent described in Patent Literature 10 has poorcompatibility with a silicone adhesive and, therefore, may separate fromthe adhesive layer after the adhesive layer is cured, which leads toinsufficient curing. Further, an adhesive tape having the adhesive layerhas a problem that a strength of bond between the adhesive layer and atape substrate is low due to the separation of the oxyalkylene solvent.

When the lithium salt described in Patent Literature 10 is added as anantistatic agent to a silicone adhesive composition, it worsens astrength of bond between the adhesive layer and a tape substrate.Therefore, in the production of an adhesive tape having the adhesivelayer on a tape substrate, it is necessary to use, as a release film puton the adhesive layer, a film which has a fluorine-modified siliconerelease agent layer which is easy to be released. Further, when theaforesaid adhesive tape is peeled from a tape-stuck body, an adhesivemay remain on the tape-stuck body and, thus, the adhesive tape may notclearly be peeled.

In view of the aforesaid circumstances, the present invention aims firstto provide a silicone adhesive which provides an adhesive layer havingan excellent antistatic property and has an excellent strength of bondto a tape substrate so that a less adhesive remains on a tape-stuck bodyafter an adhesive tape or film having the adhesive layer is peeled fromthe tape-stuck body.

The present inventor has first found that when a silicone adhesivecomposition which is addition reaction-curable comprises a compoundhaving at least two unsaturated hydrocarbon groups and two(poly)oxyalkylene residues in one molecule together with an ionic liquidcontaining no lithium, the aforesaid problems are solved. Thus, thepresent invention has been completed.

Further, the present inventor has carried out earnest research in viewof the aforesaid circumstances and found that when a silicone adhesivecomposition which is addition reaction-curable comprises a(poly)oxyalkylene compound having at least one unsaturated hydrocarbongroup in one molecule together with an ionic liquid containing nolithium, curability of the composition and an antistatic property of acured product of the composition are improved. Meanwhile, a siliconeadhesive composition which is addition reaction-curable generallycomprises a platinum group metal catalyst as a reaction catalyst. Inparticular, a reaction product of chloroplatinic acid with an olefiniccompound and a reaction product of chloroplatinic acid with a vinylgroup-containing siloxane are preferred in view of stability in storage.However, when a platinum group metal catalyst which is a complex withsuch a compound having an unsaturated hydrocarbon group is added to asilicone composition comprising an oxyalkylene compound having anunsaturated hydrocarbon group, curability of the composition is lower,compared to a composition comprising no oxyalkylene compound having anunsaturated hydrocarbon group. Thus, the silicone adhesive does notsufficiently cure by heating for a short time, in particular, for lessthan 5 minutes and, therefore, a strength of bond to a tape substrate islower. Therefore, the present invention aims secondly to provide asilicone adhesive composition which cures well by heating for a shorttime, in particular for less than 5 minutes, to give an adhesive layerhaving an excellent antistatic property.

The present inventor has secondly found that when a silicone adhesivecomposition which is addition reaction-curable comprises a compoundhaving at least one unsaturated hydrocarbon group and at least one(poly)oxyalkylene residue in one molecule, an ionic liquid containing nolithium and further, as an addition reaction catalyst, a platinum groupmetal catalyst which is not a complex with a compound having anunsaturated hydrocarbon group, the composition cures well in a shorttime to give an adhesive layer having an excellent antistatic property.Thus, the present invention has been completed.

Thus, the present invention first provides a silicone adhesivecomposition comprising

(A) an addition reaction-curable silicone,

(B1) a compound having at least two unsaturated hydrocarbon groups andtwo (poly)oxyalkylene residues in one molecule, and

(C) an ionic liquid containing no lithium.

The present invention secondly provides a silicone adhesive compositioncomprising

(A) an addition reaction-curable silicone,

(B) a compound having at least one unsaturated hydrocarbon group and atleast one (poly)oxyalkylene residue in one molecule,

(C) an ionic liquid containing no lithium, and

(e) a platinum group metal catalyst which is not a complex with acompound having an unsaturated hydrocarbon bond.

The present invention also provides an adhesive tape or film comprisinga sheet substrate of which at least one surface is laminated with acured product of the first or second silicone adhesive composition.

Effects of the Invention

The first silicone adhesive composition provides an adhesive layerhaving an excellent antistatic property and an excellent strength ofbond to the sheet substrate. The second silicone adhesive compositioncures well in a short time to give an adhesive layer having an excellentantistatic property. This silicone adhesive composition cures well byheating for a short time, in particular for less than 5 minutes, at apredetermined temperature and, therefore, is advantageous in view ofproductivity find costs. After the adhesive tape or film comprising anadhesive layer obtained from the present silicone adhesive compositionis peeled from a tape-stuck body, a less amount of the adhesivecomposition remains on the tape-stuck body. Therefore, the tape-stuckbody is not contaminated. Accordingly, the adhesive tape or film may besuitably used for masking electronic parts. Further, the adhesive tapeor film may be suitably used in situations where generation of staticelectricity is undesirable.

BEST MODE OF THE INVENTION

The present invention will be described below in detail.

First Embodiment

The first silicone adhesive composition is characterized by beingaddition reaction-curable and comprising (B1) a (poly)oxyalkylenecompound having a specific structure and (C) a specific ionic liquid.Any other components than components (B1) and (C) may be incorporated inthe silicone adhesive composition. Component (A), additionreaction-curable silicone, may be any conventional organopolysiloxane,such as an organopolysiloxane having an alkenyl group, a silicone resinand an organohydogenpolysiloxane. The characteristic components (B1) and(C) will be explained first below.

(B1) (Poly)oxyalkylene Compound

In the first embodiment according to the present invention, component(B1) is a compound having at least two unsaturated hydrocarbon groupsand two (poly)oxyalkylene residues in one molecule. One of thecharacteristics of the (poly)oxyalkylene compound is that the compoundhas at least two unsaturated hydrocarbon groups in one molecule.Accordingly, the (poly)oxyalkylene compound may react with anorganohydrogenpolysiloxane contained in the silicone adhesivecomposition to be bonded strongly in a cured product of the composition,i.e., adhesive layer. Therefore, the (poly)oxyalkylene compound does notleave the adhesive layer with time, a strength of bond between a sheetsubstrate and the adhesive layer is improved, and a tape-stuck body isless contaminated.

Another characteristic of the (poly)oxyalkylene compound (B1) is in thatthe compound has two (poly)oxyalkylene residues in one molecule. The(poly)oxyalkylene residue has a structure composed of at least oneoxyalkylene group, preferably a structure where two or more oxyalkylenegroups are bonded to each other in a linear manner. Particularly, it ispreferred that the two (poly)oxyalkylene residues are each representedby —(C₂H₄O)_(m)—(C₃H₆O)_(n)—, wherein m is a real number of 0 to 20, nis a real number of 0 to 10, m+n is 1 to 30, and (C₂H₄O) and (C₃H₆O) maybe bonded in random order. The present invention is characterized inthat the number of the (poly)oxyalkylene residue in the compound (B1) istwo in one molecule. The compound having such a structure isincorporated in the silicone adhesive composition together with theionic liquid (C) described hereinafter, so that a surface resistivity ofthe silicone adhesive layer is lowered. It is considered that this isbecause the oxyalkylene residues capture ions of the ionic liquid andefficiently cause the ions to move in the cured product, adhesive layer.To explain the decrease of the surface resistivity in more detail, acured product of a silicone adhesive composition comprising no ionicliquid nor (poly)oxyalkylene compound has a surface resistivity largerthan 1E+15 Ω/sq., i.e., 1×10¹⁵ Ω/sq., and a cured product of a siliconeadhesive composition comprising only the ionic liquid has a surfaceresistivity of 1E+13 to 1E+14 Ω/sq., i.e., 1×10¹³ to 1×10¹⁴ Ω/sq.Meanwhile, the cured product of the silicone adhesive compositioncomprising the ionic liquid and the (poly)oxyalkylene compound has asurface resistivity of 1E+9 to less than 1E+13 Ω/sq., i.e., 1×10⁹ toless than 1×10¹³ Ω/sq., preferably 1E+9 to 9.9E+12 Ω/sq., i.e., 1×10⁹ to9.9×10¹² Ω/sq., in particular, 1E+10 to 9.9E+11 Ω/sq., i.e., 1×10¹⁰ to9.9×10¹¹ Ω/sq. The surface resistivity in the present invention isdetermined according to the Japanese Industrial Standards (JIS) K6911.

In the silicone adhesive composition according to the first embodiment,if the (poly)oxyalkylene compound has only one unsaturated hydrocarbongroup, the (poly)oxyalkylene compound is not sufficiently bonded in theadhesive layer and, therefore, a strength of bond between the adhesivelayer and a sheet substrate is lower, so that an adhesive materialremains on a tape-stuck body after an adhesive tape having the adhesivelayer is peeled from the tape-stuck body, that is, a so-called residualadhesive occurs on the tape-stuck body. The residual adhesive may occureven if primer treatment is carried out to improve the strength of bondbetween the adhesive layer and the sheet substrate. If the(poly)oxyalkylene compound having at least two unsaturated hydrocarbongroups has only one (poly)oxyalkylene residue in one molecule, thesilicone adhesive composition has a less decreased surface resistivity,so that the adhesive layer does not have a sufficient antistaticproperty. It is noted that an oxyalkylene compound having oneunsaturated hydrocarbon group and one (poly)oxyalkylene residue in onemolecule may provide a good antistatic property, but at strength of bondbetween the adhesive layer and a sheet substrate is poor, because thenumber of the unsaturated hydrocarbon group is one.

The unsaturated hydrocarbon group is preferably an alkenyl group having2 to 12 carbon atoms, more preferably 2 to 10 carbon atoms. A vinylgroup and an allyl group are preferred. The (poly)oxyalkylene compoundhas at least two organic groups having the unsaturated hydrocarbon groupin one molecule. The organic group having the unsaturated hydrocarbongroup is preferably an aliphatic hydrocarbon group which has anunsaturated bond and may have an oxygen atom. Particularly, thealiphatic hydrocarbon group is preferably an alkenyl group-containingaliphatic hydrocarbon group which has 2 to 12 carbon atoms, morepreferably 2 to 10 carbon atoms and may have an oxygen atom, andincludes a vinyl group, an allyl group, a hexenyl group, an octenylgroup, an acryloylpropyl group, an acryloylmethyl group, amethacryloylpropyl group, an acryloxypropyl group, an acryloxymethylgroup, a methacryloxypropyl group, a methacryloxymethyl group, acyclohexenylethyl group, a vinyloxypropyl group, an allyloxy group andan allyloxymethyl group. Among these, an allyl group, a vinyl group, anallyloxy group and an allyloxymethyl group are preferred. A vinyl groupis preferred from the industrial viewpoint.

It is preferred that the (poly)oxyalkylene compound volatilizes hardlyat 130 degrees C. or lower and normal pressure. A (poly)oxyalkylenecompound which volatilizes at 130 degrees C. or lower volatilizes in aprocess for curing the adhesive composition and, therefore, does notremain in a cured product of the adhesive composition. As a result, thecured product may not have a good antistatic effect.

The (poly)oxyalkylene compound (B1) may be any known compound as long asthe compound has at least, two unsaturated hydrocarbon groups and two(poly)oxyalkylene residues in one molecule. The number of theunsaturated hydrocarbon groups is preferably 2 to 4, in particular, 2.Particularly, the (poly)oxyalkylene residue is preferably—(C₂H₄O)_(m)—(C₃H₆O)_(n)—. The (poly)oxyalkylene compound (B1) isparticularly one represented by the following formula (1). In theformula (1), (C₂H₄O) and (C₃H₆O) may be bonded in random order. Theformula (1) may be an average compositional formula.

In the formula (1), A is a tetravalent hydrocarbon group having 2 to 22carbon atoms, R¹ is, independently of each other, a hydrogen atom, anacyl group, or a monovalent hydrocarbon group which has 1 to 12 carbonatoms, may have an unsaturated bond and may have an oxygen atom, whereinat least two R¹'s are each an aliphatic hydrocarbon group which has 2 to12 carbon atoms and an unsaturated bond and may have an oxygen atom.

In the formula (1) m¹ and m² are, independently of each other, a realnumber of 0 to 20, and n¹ and n² are, independently of each other, areal number of 0 to 10, provided that m¹+n¹ is not zero and m²+n² is notzero. Each of m¹, m², n¹ and n² may be an average value. Preferably,m¹+n¹ is 1 to 30 and m²+n² is 1 to 30. More preferably, m¹+n¹ is 4 to 20and m²+n² is 4 to 20. In particular, m¹+n¹+m²+n² is 40 or less. If m¹,m², n¹ or n² is larger than the upper limit, the polyoxyalkylenecompound may have a larger viscosity and, therefore, poordispersibility, so that it may be difficult to uniformly disperse thecompound in the silicone adhesive composition.

The ions move easier when oxygen atoms are closer to each other.Therefore, it is particularly preferred that both of n¹ and n² in theformula (1) are zero, that is, the (poly)oxyalkylene residues do notcomprise an oxypropylene group. Such a (poly)oxyalkylene compound (B1)is represented by the formula (2):

In the formula (2), A and R¹ are as defined above, and m³ and m⁴ are,independently of each other, a real number of 1 to 20, preferably a realnumber of 1 to 10, more preferably a real number of 2 to 10. If m³ or m⁴is larger than the upper limit, the polyoxyalkylene compound may have alarger viscosity and, therefore, poor dispersibility, so that it may bedifficult to uniformly disperse the compound in the silicone adhesivecomposition.

In the formulas (1) and (2), R¹ is, independently of each other, ahydrogen atom, sin acyl group, or a monovalent hydrocarbon group whichhas 1 to 12 carbon atoms, may have an unsaturated bond and may have anoxygen atom, wherein at least two R¹'s are each an aliphatic hydrocarbongroup which has 2 to 12 carbon atoms and an unsaturated bond and mayhave an oxygen atom. The unsaturated hydrocarbon group may be thosementioned above. In particular, an allyl group, a vinyl group and anallyoxymethyl group are preferred. Examples of the monovalenthydrocarbon groups other than the unsaturated aliphatic hydrocarbongroups include alkyl groups such as a methyl group, an ethyl group, apropyl group, an isopropyl group, a butyl group and an octyl group;cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group;aryl groups such as a phenyl group, a tolyl group and a naphthyl group;aralkyl groups such as a benzyl group, a phenylethyl group and aphenylpropyl group; such groups that a part or the whole of the hydrogenatoms bonded to carbon atoms may be replaced with, for example, ahalogen atom such as fluorine, bromine and chlorine atoms, for example,halogenated monovalent hydrocarbon groups such as a trifluoropropylgroup and a chloropropyl group; and a 3-methacryloxy propyl group and a3-glycidyloxypropyl group. Among these, a methyl group is particularlypreferred. Examples of the acyl group include an acetyl group, apropionyl group, an acryloyl group, a methacryloyl group and an octanoylgroup. R¹ which is not the unsaturated aliphatic hydrocarbon groups ispreferably a hydrogen atom.

In the formulas (1) and (2), A is a tetravalent hydrocarbon group having2 to 22 carbon atoms. The tetravalent hydrocarbon group is preferably alinear or branched, aliphatic saturated hydrocarbon group having 2 to16, preferably 2 to 8, carbon atoms, or a cyclic hydrocarbon group whichhas 6 to 22, preferably 6 to 14, carbon atoms and may have a branchedchain. Examples of the linear or branched, tetravalent aliphaticsaturated hydrocarbon group include those represented by the followingformulas:

In the formulas, n is, independently of each other, an integer of 1 to8. Examples of the tetravalent cyclic hydrocarbon group include thoserepresented by the following formulas:

In the formulas, n is, independently of each other, an integer of 1 to8.

Examples of the (poly)oxyalkylene compound (B1) include the following:(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₆—(C₃H₆O)₁—H]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₂—H]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₃H₆O)₈—H]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₈—CH₃]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₁₆—CH₃]₂(CH₂═CH—CH₂—O—)₂—C₆H₂—[O—(C₂H₄O)₆—(C₃H₆O)₁—H]₂CH₂═CH—CH₂—(OC₂H₄)₆—O—CH₂—CH₂—CH₂—O—(C₂H₄O)₅—CH₂—CH═CH₂

An amount of component. (B1) in the silicone adhesive compositionaccording to the first embodiment is preferably 0.27 to 3.3 parts bymass, more preferably 0.3 to 3 parts by mass, most preferably 0.6 to 1.8parts by mass, relative to 100 parts by mass of the additionreaction-curable silicone contained in the silicone adhesivecomposition. If the amount is less than the lower limit, the effect ofproviding an antistatic property is not sufficiently attained. If theamount is larger than the upper limit, an adhesion strength andcurability of the silicone adhesive composition may be lower and astrength of bond to a sheet substrate may be lower. The additionreaction-curable silicone is a siloxane contained in any conventionalsilicone adhesive composition, such as an organopolysiloxane having analkenyl group, an organohydrogenpolysiloxane and a silicone resin. Theamount of component (B1) is preferably such that a ratio of the totalnumber of the SiH groups in the silicone adhesive composition to thetotal number of the unsaturated hydrocarbon groups in component (B1) andthe silicone adhesive composition is 1 to 20, more preferably 1 to 15.As a result, component (B1) is bonded strongly in the adhesive layerand, therefore, the aforesaid residual adhesive is avoided.

(C) Ionic Liquid

The ionic liquid is a salt composed of an anion and a cation, andrepresented by Z⁺Y⁻ wherein Z is a cation and Y is an anion. Ascomponent (C) In the present invention, any conventional ionic liquidmay be used. The ionic liquid is generally a molten salt at roomtemperature. However, any conventional ionic liquid which is a solidsalt at room temperature may also be used. The ionic liquid functions asan antistatic agent. Thus, ions of the ionic liquid move in a curedproduct obtained by curing the present silicone composition, i.e.,adhesive layer, to decrease a surface resistivity of the product. PatentLiterature 10 describes a lithium salt as an antistatic agent. However,when lithium is contained in a silicone adhesive composition, corrosionof a tape-stuck body to which an adhesive layer obtained from thecomposition is adhered increases; a strength of bond to a sheetsubstrate is insufficient, even if a primer is used; and an adhesivematerial remains on the tape-stuck body when an adhesive tape obtainedwith the adhesive composition is peeled from the tape-stuck body, thatis, a residual adhesive occurs. Therefore, the lithium salt is notsuitable. Examples of the lithium salt include LiBF₄, LiClO₄, LiPF₆,LiAsF₆, LiSbF₆, LiSO₃CF₃, LiN(SO₂CF₃)₂, LiSO₃C₄F₉, LiC(SO₂CF₃)₃ andLiB(C₆H₅)₄. Some of them are known as ionic liquids. However, component(C) in the present invention is an ionic liquid containing no lithium.

The ionic liquid in the present invention is preferably at least oneselected from the group consisting of quaternary ammonium salts,quaternary phosphonium salts, imidazolium salts, pyridinium salts andpyrrolidinium salts. Thus, the cation (Z⁺) is selected from the groupconsisting of quaternary ammonium cations, quaternary phosphoniumcations, imidazolium cations, pyridinium cations and pyrrolidiniumcations. In particular, quaternary ammonium salts are preferred. Theanion (Y⁻) of the ionic liquid is not limited to any particular one, andmay be any anions of conventional ionic liquids.

Examples of the anion (Y⁻) include halide ions, a cyanide ion, adicyanoamine anion, a trifluoromethanesulphonate ion, anonafluorobutansulphonate ion, a tetrafluoroethanesulphonate ion, alactate ion, a salicylate ion, a thiosalicylate ion, a dibutylphosphateion, an acetate ion, a hexafluoroantimonate ion, a hydrogensulfate ion,a sulfate ion, an octylsulphonate ion, a tetrachloroaluminate ion, athiocyanate ion, a tris(trifuluoromethylsulphonyl)methide ion, anaminoacetate ion, an aminopropiante ion, a diethylphosphate ion, adimethylphophate ion, an ethylsulfate ion, a methylsulfate ion, ahydroxide ion, a bis(trimethylpentyl)phosphinate ion, a decanoate ion, atrifluoroacetate ion, a ferrate ion, a tetrafluoroborate ion, ahexafluorophosphate ion, a sulfonylamide ion, a butansulphonate ion, amethylsulphonate ion, an ethylsulphonate ion, abis(trifluoromethylsulfonyl)imide anion, abis(trifluoroethylsulfonyl)imide anion and abis(pentafluoroethylsulfonyl)imide anion. Among these, abis(trifluoromethylsulfonyl)imide anion is preferred.

Examples of the ionic liquid include the following salts:

-   butyltrimethylammonium bis(trifluoromethanesulfonyl)imide,-   ethyldimethylpropylammonium bis(trifluoromethane sulfonyl)imide,-   2-hydroxymethyl-trimethylammonium L-(+)-lactate,-   methyltrioctylammonium bis(trifluoromethanesulfonyl)imide,-   methyltrioctylammonium thiosalicylate,-   tetrabutylammonium nonafluorobutanesulfonate,-   tetramethylammonium trifluoromethanesulfonate,-   tetraheptylammonium chloride,-   tributylmethylammonium dibutylphosphate,-   tributylmethylammonium methylsulfate,-   triethylmethylammonium dibutylphosphate,-   tris(2-hydroxyethyl)methylammonium methylsulfate,-   1-allyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-allyl-3-methylimidazolium bromide,-   1-allyl-3-methylimidazolium chloride,-   1-allyl-3-methylimidazolium dicyanamide,-   1-allyl-3-methylimidazolium iodide,-   1-benzyl-3-methylimidazolium chloride,-   1-benzyl-3-methylimidazolium hexafluorophosphate,-   1-benzyl-3-methylimidazolium tetrafluoroborate,-   1,3-bis(cyanomethyl)imidazolium bis(trifluoromethanesulfonyl)imide,-   1,3-bis(cyanomethyl)imidazolium chloride,-   1,3-bis(cyanomethyl)imidazolium bis(trifluoromethanesulfonyl)imide,-   1,3-bis(cyanopropyl)imidazolium chloride,-   1-butyl-2,3-dimethylimidazolium chloride,-   1-butyl-2,3-dimethylimidazolium hexafluorophosphate,-   1-butyl-2,3-dimethylimidazolium tetrafluoroborate,-   4-(3-butyl-1-imidazoilio)-1-butanesulfonate,-   1-butyl-3-methylimidazolium acetate,-   1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-butyl-3-methylimidazolium bromide,-   1-butyl-3-methylimidazolium chloride,-   1-butyl-3-methylimidazolium dibutylphosphate,-   1-butyl-3-methylimidazolium dicyanamide,-   1-butyl-3-methylimidazolium hexafluoroantimonate,-   1-butyl-3-methylimidazolium hexafluorophosphate,-   1-butyl-3-methylimidazolium hydrogen sulfate,-   1-butyl-3-methylimidazolium iodide,-   1-butyl-3-methylimidazolium methanesulfonate,-   1-butyl-3-methylimidazolium nitrate,-   1-butyl-3-methylimidazolium octyl sulfate,-   1-butyl-3-methylimidazolium tetrachloroaluminum,-   1-butyl-3-methylimidazoliuim tetrafluoroborate,-   1-butyl-3-methylimidazolium thiocyanate,-   1-butyl-3-methylimidazolium trifluoroacetate,-   1-butyl-3-methylimidazolium trifluoromethanesulfonate,-   1-(3-cyanopropyl)-3-methylimidazolium bis(trifluoromethane    sulfonyl)amide,-   1-(3-cyanopropyl)-3-methylimidazolium dicyanamide,-   1-decyl-3-methylimidazolium chloride,-   1-decyl-3-methylimidazolium tetrafluoroborate,-   1,3-diethoxyimidazolium bis(trifluoromethanesulfonyl)imide,-   1,3-diethoxyimidazolium hexafluorophosphate,-   1,3-dihydroxyimidazolium bis(trifluoromethanesulfonyl)imide,-   1,3-dihydroxy-2-methylimidazolium    bis(trifluoromethanesulfonyl)imide,-   1,3-dimethoxyimidazolium bis(trifluoromethanesulfonyl)imide,-   1,3-dimethoxyimidazolium hexafluorophosphate,-   1,3-dimethoxy-2-methylimidazolium bis(trifluoromethylsulfonyl)imide,-   1,3-dimethoxy-2-methylimidazolium hexafluorophosphate,-   1,3-dimethylimidazolium dimethyl phosphate,-   1,3-dimethylimidazolium methanesulfonate,-   1,3-dimethylimidazolium methyl sulfate,-   1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imide,-   1,2-dimethyl-3-propylimidazolium    tris(trifluoromethylsulfonyl)methide,-   1-dodecyl-3-methylimidazolium iodide,-   1-ethyl-2,3-dimethylimidazolium chloride,-   1-ethyl-2,3-dimethylimidazolium hexafluorophosphate,-   1-ethyl-2,3-dimethylimidazolium tetrafluoroborate,-   1-ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate,-   1-ethyl-3-methylimidazolium acetate,-   1-ethyl-3-methyldimidazolium aminoacetate,-   1-ethyl-3-methylimidazolium (S)-2-aminopropionate,-   1-ethyl-3-methylimidazolium bis(pentafluoroethylsulfonyl)imide,-   1-thyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-ethyl-3-methylimidazolium bromide,-   1-ethyl-3-methylimidazolium chloride,-   1-ethyl-3-methylimidazolium dibutyl phosphate,-   1-ethyl-3-methylimidazolium dicyanamide,-   1-ethyl-3-methylimidazolium diethyl phosphate,-   1-ethyl-3-methylimidazolium dimethyl phosphate,-   1-ethyl-3-methylimidazolium ethyl sulfate,-   1-ethyl-3-methylimidazolium hexafluorophosphate,-   1-ethyl-3-methylimidazolium hydrogen sulfate,-   1-ethyl-3-methylimidazolium hydroxide solution,-   1-ethyl-3-methylimidazolium iodide,-   1-ethyl-3-methylimidazolium L-(+)-lactate,-   1-ethyl-3-methylimidazolium methyl sulfate,-   1-ethyl-3-methylimidazolium nitrate,-   1-ethyl-3-methylimidazolium tetrachloroaluminum,-   1-ethyl-3-methylimidazolium tetrafluoroborate,-   1-ethyl-3-methylimidazolium-   1,1,2,2-tetrafluoroethanesulfonate,-   1-ethyl-3-methylimidazolium thiocyanate,-   1-ethyl-3-methylidazolium trifluoromethanesulfonate,-   1-hexyl-3-methylimidazolium chloride,-   1-hexyl-3-methylimidazolium hexafluorophosphate,-   1-hexyl-3-methylimidazolium iodide,-   1-hexyl-3-methylimidazolium tetrafluoroborate,-   1-hexyl-3-methylimidazolium trifluoromethansulfonate,-   1-(2-hydroxyethyl)-3-methylimidazolium dicyanamide,-   1-methylimidazolium chloride,-   1-methylimidazolium hydrogen sulfate,-   1-methyl-3-octylimidazolium chloride,-   1-methyl-3-octylimidazolium hexafluorophosphate,-   1-methyl-3-octylimidazolium tetrafluoroborate,-   1-methyl-3-octylimidazolium trifluoromethanesulfonate,-   1-methyl-3-propylimidazolium iodide,-   1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide,-   1,2,3-trimethylimidazolium methylsulfate,-   1,2,3-trimethylimidazolium trifluoromethanesulfonate,-   tetrabutylphosphonium methanesulfonate,-   tributylmethylphosphonium dibutyl phosphate,-   tributylmethylphosphonium methyl sulfate,-   triethylmethylphosphonium dibutyl phosphate,-   trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl) amid,-   trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)    phosphinate,-   trihexyltetradecylphosphonium bromide,-   trihexyltetradecylphosphonium chloride,-   trihexyltetradecylphosphonium decanoate,-   trihexyltetradecylphosphonium dicyanamide,-   3-(triphenylphosphinate)propane-1-sulfonate,-   1-butyl-4-methylpyridinium bromide,-   1-butyl-4-methylpyridinium chloride,-   1-butyl-4-methylpyridinium hexafluorophosphate,-   1-butyl-4-methylpyridinium iodide,-   1-butyl-4-methylpyridinium tetrafluoroborate,-   1-butylpyridinium bromide,-   1-(3-cyanopropyl)pyridinium chloride,-   1-ethylpyridinium tetrafluoroborate,-   3-methyl-1-propylpyridinium bis(trifluormethylsulfonyl)imide,-   1-butyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide,-   1-butyl-1-methylpyrrolidinium bromide,-   1-butyl-1-methylpyrrolidinium dicyanamide,-   1-butyl-1-methylpyrrolidinium hexafluorophosphate,-   1-butyl-1-methylpyrrolidinium iodide,-   1-butyl-1-methylpyrrolidinium tetrafluoroborate,-   1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate,-   1-ethyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide,-   1-ethyl-1-methylpyrrolidinium bromide,-   1-ethyl-1-methylpyrrolidinium hexafluorophosphate,-   1-ethyl-1-methylpyrrolidinium tetrafluoroborate,-   1-butyl-1-methylpiperidinium bis(trifluoromethanesulfonyl)imide,-   1-butyl-1-methylpiperidinium hexafluorophosphate,-   1-butyl-1-methylpiperidinium tetrafluoroborate,-   triethylsulfonium bis(trifluoromethanesulfonyl)imide,-   1-ethyl-3-methylimidazolium methanesulfonate,-   methyl-tri-n-butylammonium methylsulfate,-   1,2,4-trimethylpyrazolium methylsulfate,-   1-ethyl-2,3-di-methylimidazolium ethylsulfate,-   methylimidazolium chloride,-   methylimidazolium hydrogensulfate,-   1-ethyl-3-methylimidazolium tetrachloroaluminum,-   1-ethyl-3-methylimidazolium ethylsulfate,-   1-butyl-3-methylimidazolium methylsulfate,-   choline acetate,-   choline salicylate,-   methyltrioctylammonium hexafluorophosphate,-   tetrabutylphosphonium bis(trifluoromethanesulfonyl)imide,-   tributyldodecylphosphonium bis(trifluoromethanesulfonyl)imide,-   trimethylhexylammonium bis(trifluoromethanesulfonyl)imide,-   trimethylpropylammonium bis(trifluoromethanesulfonyl)imide,-   1-octyl-4-methylpyridinium bis(trifluoromethanesulfonyl)imide,-   1-hexyl-4-methylpyridinium hexafluorophosphate,-   1-hexyl-4-methylpyridinium bis(trifluoromethanesulfonyl)imide,-   1,2-dimethyl-3-propylimidazolium iodide,-   1-ethyl-3-methylimidazolium trifluoroacetate,-   1-butyl-3-methylimidazolium tetrachloroferrate(III),-   1-methyl-1-propylpiperidinium bis(trifluoromethanesulfonyl) imide,-   1-butylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-butyl-3-methylpyridinium bis(trifluoromethanesulfonyl)imide,-   1-butyl-4-methylpyridinium bis(trifluoromethanesulfonyl)imide,-   1-methyl-1-pyrrolidinium bis(trifluoromethanesulfonyl) imide,-   1-butyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl) imide,-   1-butyl-1-methylpyrrolidinium chloride,-   1-methyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-hexyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-butyl-2,3-dimethylimidazolium bis(trifluoromethanesulfonyl)imide,-   1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imide,-   1-methyl-3-octylimidazolium tetrafluoroborate,-   1-(3-hydroxypropyl)-3-methylimidazolium tetrafluoroborate,-   1-butylpyridinium hexafluorophosphate,-   1-butyl-3-methylpyridinium hexafluorophosphate,-   1-butylpyridinium tetrafluoroborate,-   1-butyl-3-methylpyridinium tetrafluoroborate,-   1-butylpyridinium chloride,-   tributylmethylammonium bis(trifluoromethanesulfonyl)imide,-   tetrabutylammonium hexafluorophosphate,-   tetrabutylammonium bromide,-   tetrapentylammonium bromide,-   tetrabutylphosphonium hexafluorophosphate, and-   tributylmethylphosphonium iodide.

Among these, ionic liquids whose anions are abis(trifluoromethylsulfonyl)imide anion are particularly preferred,because curing of the silicone adhesive composition is less hindered.

In particular, salts composed of a quaternary ammonium cation and abis(trifluoromethylsulfonyl)imide anion are preferred, because curing ofthe silicone adhesive composition is least hindered. Examples of suchionic liquids include the following salts:

-   butyltrimethylammonium bis(trifluoromethanesulfonyl)imide,-   ethyldimethylpropylammonium bis(trifluoromethanesulfonyl)imide,-   methyltrioctylammonium bis(trifluoromethanesulfonyl)imide,-   trimethylhexylammonium bis(trifluoromethanesulfonyl)imide,-   trimethylpropylammonium bis(trifluoromethanesulfonyl)imide, and-   tributylmethylammonium bis(trifluoromethanesulfonyl)imide.

The ionic liquid may be used as such in the silicone adhesivecomposition, or in such a manner that the ionic liquid is diluted withan organic solvent or that the ioninc liquid is dispersed in a siliconeoil to be pasty. However, the ionic liquid may be used in any othermanner.

An amount of component (C) is preferably 0.003 to 1.5 parts by mass,more preferably 0.006 to 1.2 parts by mass, still more preferably 0.06to 1.2 parts by mass, particularly 0.06 to 0.6 part by mass, relative to100 parts by mass of the addition reaction-curable silicone contained inthe silicone adhesive composition. If the amount is less than the lowerlimit, the effect of providing an antistatic property is notsufficiently attained. If the amount is larger than the upper limit, anadhesion strength and curability of the silicone adhesive compositionmay be lower and a strength of bond to a sheet substrate may be lower.

First Silicone Adhesive Composition which is Addition Reaction-Curable

Components other than components (B1) and (C) contained in the firstsilicone adhesive composition which is addition reaction-curable may becomponents contained in conventional silicone adhesive compositionswhich are addition reaction-curable, as mentioned above. For example,the addition reaction-curable silicone (A) may be the following (a) to(c), and further the following components (d) and (e) may beincorporated:

(a) a linear diorganopolysiloxane having two or more alkenyl groups inone molecule,

(b) an organopolysiloxane having R⁴ ₃SiO_(0.5) units and SiO₂ units in amole ratio of the R⁴ ₃SiO_(0.5) units to the SiO₂ units of 0.6 to 1.7,wherein R⁴ is a monovalent hydrocarbon group having 1 to 10 carbonatoms,

(c) an organopolyslloxane having two or more SiH groups in one molecule,

(d) optionally a reaction inhibitor, and

(e′) a catalyst for an addition reaction.

Components (a) to (d) and (e′) will be described below in more detail.

(a) Linear Diorganopolysiloxane Having Alkenyl Groups

Any linear diorganopolysiloxane may be used as long as it has two ormore alkenyl groups in one molecule.

The diorganopolysiloxane may be oily or raw rubber-like. The oilydiorganopolysiloxane preferably has a viscosity of 1000 mPa·s or more,in particular 10,000 mPa·s or more, at 25 degrees C. If the viscosity isless than the lower limit, curability of the adhesive composition islower, and cohesion, i.e., a strength of bond to a sheet substrate, islower. In a case of the raw rubber-like diorganopolysiloxane, aviscosity of a 30% solution of it in toluene is preferably 100,000 mPa·sor less at 25 degrees C. If the viscosity is larger than 100,000 mPa·s,a viscosity of the composition is too high, so that it is difficult tostir the composition in its preparation. The viscosity is determinedwith a BM type rotary viscometer. Two or more of thediorganopolysiloxane may be used in combination.

The linear diorganopolysiloxane having alkenyl groups is represented,for example, by the following formula (8) or (9).R² _((3−a))X_(a)SiO—(R²XSiO)_(p)—(R² ₂SiO)_(q)—SiR² _((3−a))X_(a)  (8)R² ₂(OH)SiO—(R²XSiO)_(p+2)—(R² ₂SiO)_(q)—SiR² ₂(OH)  (9)In the formulas, R² is, independently of each other, a monovalenthydrocarbon group having no aliphatic unsaturated bond, X is an organicgroup having an alkenyl group, a is an integer of 0 to 3, preferably 1,p is an integer of zero or larger, and q is an integer of 100 or larger,provided that at least one of a and p is not zero. p+q is such that aviscosity of the diorganopolysiloxane is 1,000 mPa·s or more at 25degrees C.

R² is preferably a monovalent hydrocarbon group which has 1 to 10 carbonatoms, preferably 1 to 7 carbon atoms, and has no aliphatic unsaturatedbond. Examples of the monovalent hydrocarbon group include alkyl groupssuch as a methyl group, an ethyl group, a propyl group and a butylgroup; cycloalkyl groups such as a cyclohexyl group; and aryl groupssuch as a phenyl group and a tolyl group. In particular, a methyl groupand a phenyl group are preferred.

X is preferably an organic group which has 2 to 10 carbon atoms and analkenyl group, and includes a vinyl group, an allyl group, a hexenylgroup, an octenyl group, an acryloylpropyl group, an acryloylmethylgroup, a methacryloylpropyl group, an acryloxypropyl group, anacryloxymethyl group, a methacryloxypropyl group, a methacryloxymethylgroup, a cyclohexenylethyl group and a vinyloxypropyl group. Amongthese, a vinyl group is preferred from the industrial viewpoint.

(b) Organopolysiloxane Having M Units and Q Units

The organopolysiloxane has R⁴ ₃SiO_(0.5) units and SiO₂ units and may beany conventional one. The organopolysiloxane preferably has R⁴₃SiO_(0.5) units and SiO₂ units in a mole ratio of the R⁴ ₃SiO_(0.5)units to the SiO₂ units of 0.6 to 1.7, more preferably 0.7 to 1.3. R⁴ isa monovalent hydrocarbon group having 1 to 10 carbon atoms, and may bethose mentioned above for R². If the mole ratio of R⁴ ₃SiO_(0.5) unitsto the SiO₂ units is less than the lower limit, an adhesion strength anda tackiness of the adhesive layer may be too low. If the ratio is largerthan the upper limit, an adhesion strength of the adhesive layer and astrength of bond to a sheet substrate may be lower. Theorganopolysiloxane may have an OH group. A content of the OH group ispreferably 4.0% by mass or less, relative to a mass of theorganopolysiloxane. If the content is larger than the upper limit,curability of the adhesive layer may be lower.

Two or more of the organopolysiloxane may be used in combination.Further, the organopolysiloxane may have R⁴SiO_(1.5) units and/or R⁴₂SiO units as long as the effects of the present invention are notobstructed.

Components (a) and (b) may be simply mixed with each other and used. Ina case where an organopolysiloxane represented by the formula (9) isused as component (a), components (a) and (b) may be reacted with eachother to obtain a condensation reaction product and used. Thecondensation reaction may be carried out by dissolving a mixture ofcomponents (a) and (b) in a solvent such as toluene and reacting thecomponents with each other in the presence of an alkaline catalyst in arange from room temperature to a reflux temperature.

A mass ratio of component, (a) to component (b) may be 20/80 to 100/0,preferably 30/70 to 95/5. If the amount of component (a) is less thanthe lower limit, an adhesion strength of the adhesive layer and astrength of bond to a sheet substrate are lower.

(c) Organohydrogenpolysioxane

The organohydrogenpolysiloxane is a crosslinking agent and has at leasttwo, preferably three or more, SiH groups. Theorganohydrogenpolysiloxane may be linear, branched or cyclic. Theorganohydrogenpolysiloxane preferably has a viscosity at 25 degrees C.of 1 to 5,000 mPa·s, more preferably 5 to 500 mPa·s. The viscosity isdetermined with a BM type rotary viscometer. Theorganohydrogenpolysiloxane may be any conventional one.

The organohydrogenpolysiloxane includes, for example, linear siloxanesrepresented by the following formula (6) and cyclic siloxanesrepresented by the following formula (7).

In the formulas, R³ is a monovalent hydrocarbon group having 1 to 10carbon atoms, b is 0 or 1, r and s are each such an integer that theviscosity of the organohydrogenpolysiloxane at 25 degrees C. is 1 to5,000 mPa·s, more preferably 5 to 500 mPa·s, t is an integer of 2 orlarger, v is an integer of 0 or larger, provided that t+v □ 3,preferably 8 □ t+v □ 3. Two or more of the organohydrogenpolysiloxanemay be used in combination.

R³ is a monovalent hydrocarbon group having 1 to 10 carbon atoms,preferably 1 to 7 carbon atoms, and includes alkyl groups such as amethyl group, an ethyl group, a propyl group and a butyl group;cycloalkyls such as a cyclohexyl group; aryl groups such as a phenylgroup and a tolyl group; and alkenyl groups such as a vinyl group and anallyl group. In particular, a methyl group and a phenyl group arepreferred.

An amount of the organohydrogenpolysiloxane is preferably such that aratio of the number of SiH groups in component (c) to the number ofalkenyl groups in component (a) is 1 to 20, in particular, 1 to 15. Ifthe amount is less than the lower limit, a degree of cross linking in acured product of the adhesive composition is lower and, therefore, astrength of bond to a sheet substrate may be lower. If the amount islarger than the upper limit, a degree of crosslinking of the curedproduct is too high and, therefore, the adhesive layer may not have asufficient adhesion strength nor a sufficient tackiness. Further, a timeperiod for the adhesive composition (composition bath) to be usable maybe shorter. As mentioned above, the present silicone adhesivecomposition comprises (poly)oxyalkylene compound (B1) which hasunsaturated hydrocarbon groups. A ratio of the number of SiH groups incomponent (c) to the number of unsaturated hydrocarbon groups incomponents (B1) and (a) is preferably 1 to 20, more preferably 1 to 15.As a result, component (B1) is bonded strongly in the adhesive layerand, therefore, a residual adhesive is avoided as mentioned above.

(d) Reaction Inhibitor

The silicone adhesive composition may comprise a reaction inhibitor asan optional component. When the silicone adhesive composition isprepared, applied on a sheet substrate and, then, heated to be cured,the reaction inhibitor works to prevent increase of a viscosity andgelation of the composition before heat curing. The reaction inhibitormay be any conventional one. Examples of the reaction inhibitor include3-methyl-1-butyn-3-ol, 3-methyl-1-penthyn-3-ol,3,5-dimethyl-1-hexyn-3-ol, 1-ethynylcyclohexanol,3-methyl-3-trimethylsiloxy-1-butyne,3-methyl-3-trimethylsiloxy-1-penthyne,3,5-dimethyl-3-trimethylsiloxy-1-hexyne,1-ethynyl-1-trimethylsiloxycyclohexane,bis(2,2-dimethyl-3-butynoxy)dimethylsilane,1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane and1,1,3,3-tetramethyl-1,3-divinyldisiloxane.

An amount of the reaction inhibitor is 0 to 8 parts by mass, preferably0.01 to 8 parts by mass, in particular, 0.05 to 2 parts by mass,relative to total 100 parts by mass of components (a) and (b). If theamount is larger than the upper limit, curability of the composition maybe lower.

(e′) Addition Reaction Catalyst

The addition reaction catalyst according to the first embodiment is toaccelerate an addition reaction of components (a) and (B1) withcomponent (c), and may be any conventional one. A platinum group metalcatalyst is preferred. Examples of the platinum group metal catalystinclude platinum catalysts, palladium catalysts, rhodium catalysts andruthenium catalysts. Among these platinum catalysts are preferred.Examples of the platinum catalysts include chloroplatinic acid, asolution of chloroplatinic acid in an alcohol, a reaction product ofchloroplatinic acid with an alcohol, a reaction product ofchloroplatinic acid with an olefinic compound, and a reaction product ofchloroplatinic acid with a vinyl group-containing siloxane. A reactionproduct of chloroplatinic acid with an olefinic compound and a reactionproduct of chloroplatinic acid with a vinyl group-containing siloxaneare preferred in view of stability in storage.

An amount of the catalyst may be a catalytic amount, i.e., an amounteffective in accelerating the addition reaction of components (a) and(B1) with component (c). In particular, the amount is preferably suchthat an amount of a platinum group metal is 1 to 5,000 ppm, particularly5 to 1,000 ppm, relative to a total amount by mass of components (a),(B1) and (b). If the amount is less than the lower limit, curability ofthe silicone adhesive composition is lower and a degree of crosslinkingof a cured product of the composition is lower, so that a strength ofbond to a sheet substrate may be lower. If the amount is larger than theupper limit, the composition in a bath is usable only for a shorterperiod of time.

The present silicone adhesive composition may be prepared by addingcomponents (B1) and (C) to a commercially available silicone adhesivecomponent which is addition reaction-curable. Examples of thecommercially available silicone adhesive component include KR-3700,KR-3701, KR-3704, X-40-3237 and KR-3706, ex Shin-Etsu Chemical Co. Ltd.When components (B1) and (C) are added to a commercially availablesilicone adhesive component, it may happen that the ratio of the totalnumber of SiH groups to the total number of unsaturated hydrocarbongroups in the composition be outside the afore-mentioned range. In thatcase, the organohydrogenpolysiloxane (c) may be added to adjust theratio.

Second Embodiment

The present silicone adhesive composition according to the secondembodiment is addition reaction-curable, and characterized first bycomprising (B) a (poly)oxyalkylene compound having a specific structureand (C) a specific ionic liquid, and second by comprising, as anaddition reaction catalyst, (e) a platinum group metal catalyst which isnot a complex with a compound having an unsaturated hydrocarbon bond.Any other components than components (B), (C) and (e) may beincorporated in the silicone adhesive composition. Component (A),addition reaction-curable silicone, may be any conventionalorganopolysiloxane, such as an organopolysiloxane having an alkenylgroup, a silicone resin and an organohydogenpolysiloxane. Thecharacteristic components (B), (C) and (e) will be explained firstbelow.

(B) (Poly)oxyalkylene Compound

In the second embodiment according to the present invention, component(B) is a compound having at least one unsaturated hydrocarbon group andat least one (poly)oxyalkylene residue in one molecule. One of thecharacteristics of component (B) in the second embodiment is that thecompound has at least one unsaturated hydrocarbon group in one molecule.Accordingly, the compound is compatible in the silicone adhesivecomposition which is addition reaction-curable, and may react with theorganohydrogenpolysiloxane contained in the composition to be bonded ina cured product of the composition. Therefore, the (poly)oxyalkylenecompound does not leave from the adhesive layer with time, and atape-stuck body is less contaminated.

Another characteristic of component (B) is in that component (B) has atleast one (poly)oxyalkylene residue in one molecule. The(poly)oxyalkylene residue is preferably one represented by—(C₂H₄O)_(m)—(C₃H₆O)_(n)—, wherein m is a real number of 0 to 20, n is areal number of 0 to 10, m+n is 1 to 30, and (C₂H₄O) and (C₃H₆O) may bebonded in random order. The oxyalkylene compound having such a structureis incorporated in the silicone adhesive composition together with theionic liquid (C) described hereinafter, so that a surface resistivity ofthe silicone adhesive layer is lowered. It is considered that this isbecause the oxyalkylene residues capture ions of the ionic liquid andefficiently cause the ions to move in the cured product, adhesive layer.To explain the decrease of the surface resistivity in more detail, acured product of a silicone adhesive composition comprising no ionicliquid nor (poly)oxyalkylene compound has a surface resistivity largerthan 1E+15 Ω/sq., i.e., 1×10¹⁵ Ω/sq., and a cured product of a siliconeadhesive composition comprising only the ionic liquid has a surfaceresistivity of 1e+13 to 1E+14 Ω/sq., i.e., 1×10¹³ to 1×10¹⁴ Ω/sq.Meanwhile, the cured product of the silicone adhesive compositioncomprising the ionic liquid and the (poly)oxyalkylene compound has asurface resistivity of 1E+9 to less than 1E+13 Ω/sq., i.e., 1×10⁹ toless than 1×10¹³ Ω/sq. The surface resistivity in the present inventionis determined according to Japanese Industrial Standards (JIS) K6911.Preferably, component (B) in the second embodiment of the presentinvention has one or two (poly)oxyalkylene residues in one molecule.

The unsaturated hydrocarbon group is preferably an alkenyl group having2 to 12 carbon atoms, more preferably 2 to 10 carbon atoms. A vinylgroup and an allyl group are preferred. The (poly)oxyalkylene compoundhas at least one organic group having the unsaturated hydrocarbon groupin one molecule. Examples of the unsaturated hydrocarbon group may bethose mentioned above for component (B1).

It is preferred that the (poly)oxyalkylene compound volatilizes hardlyat 130 degrees C. or lower and normal pressure. A (poly)oxyalkylenecompound which volatilizes at 130 degrees C. or lower voltilize in aprocess of curing an adhesive composition and, therefore, does notremain in a cured product of the adhesive composition. As a result, thecured product may not have a good antistatic effect.

Component (B) is preferably a compound having at least two unsaturatedhydrocarbon groups and two (poly)oxyalkylene residues in one molecule(hereinafter referred to as compound (B1)), which is the same ascompound (B1) in the first embodiment. The number of the unsaturatedhydrocarbon groups is preferably 2 to 4, in particular, 2. The compound(B1) is represented by the following formula (1). In the formula (1),(C₂H₄O) and (C₃H₆O) may be bonded in random order. The formula (1) maybe an average compositional formula.

The compound represented by the formula (1) is as explained in theaforesaid first embodiment. A, R¹, m¹, m², n¹ and n² are as definedabove.

The ions move easier when oxygen atoms are closer to each other.Therefore, it is particularly preferred that both of n¹ and n² in theformula (1) are zero, that is, the (poly)oxyalkylene compound (B1) doesnot comprise an oxypropylene group. Such a (poly)oxyalkylene compound isrepresented by the formula (2):

The compound represented by the formula (2) is as explained in theaforesaid first embodiment. A, R¹, m³ and m⁴ are as defined above.

Examples of the (poly)oxyalkylene compound (B1) include the following:(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₆—(C₃H₂O)₁—H]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₂—H]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₃H₆O)₈—H]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₈—CH₃]₂(CH₂═CH—CH₂—O—CH₂—)₂—C—[CH₂—O—(C₂H₄O)₁₆—CH₃]₂(CH₂═CH—CH₂—O—)₂—C₆H₂—[O—(C₂H₄O)₆—(C₃H₆O)₁—H]₂CH₂═CH—CH₂—(OC₂H₄)₅—O—CH₂—CH₂—CH₂—O—(C₂H₄O)₅—CH₂—CH═CH₂

It is also preferred that component (B) in the second embodiment is acompound having at least one unsaturated hydrocarbon group and one(poly)oxyalkylene residue in one molecule (hereinafter referred to ascompound (B2)). The compound (B2) is particularly one represented by thefollowing formula (3), In the formula (3), (C₂H₄O) and (C₃H₆O) may bebonded in random order. The formula (3) may be an average compositionalformula.R³—O—(C₂H₄O)_(m5)—(C₃H₆O)_(n5)R²  (3)In the formula (3), R³ is a monovalent apliphatic hydrocarbon groupwhich has 2 to 12 carbon atoms and an unsaturated bond, R² is a hydrogenatom, a saturated monovalent hydrocarbon group having 1 to 8 carbonatoms, or a group as defined for R³, m⁵ is a real number of 0 to 20, andn⁵ is a real number of 0 to 10, provided that m⁵+n⁵ is not zero.

In the formula (3), m⁵ is a real number of 0 to 20, and n⁵ is a realnumber of 0 to 10, provided that m⁵+n⁵ is not zero. Each of m⁵ and n⁵may be an average value. Preferably, m⁵+n⁵ is 1 to 30, more preferably 4to 20. If m⁵ or n⁵ is larger than the upper limit, the polyoxyalkylenecompound may have a larger viscosity and, therefore, poordispersibility, so that it may be difficult to uniformly disperse thecompound in the silicone adhesive composition.

The ions move easier when oxygen atoms are closer to each other.Therefore, it is particularly preferred that n⁵ in the formula (3) iszero, that is, the (poly)oxyalkylene compound (B2) does not comprise anoxypropylene group. Such a (poly)oxyalkylene compound is represented bythe formula (4):R³—O—(C₂H₄O)_(m5)—R²  (4)In the formula (4), R² and R³ are as defined above, and m⁵ is a realnumber of 1 to 20, preferably a real number of 1 to 10, more preferablya real number of 2 to 10. When m⁵ is larger, compatibility of the(poly)oxyalkylene compound with a silicone adhesive is poorer, so thatthe adhesive composition may not sufficiently cure. Further, the(poly)oxyalkylene compound has a larger viscosity and, therefore, it maybe difficult to uniformly disperse the compound in the silicone adhesivecomposition.

In the formulas (3) and (4), R³ is a monovalent hydrocarbon group whichhas 1 to 12 carbon atoms and an unsaturated bond, R² is a hydrogen atom,a saturated monovalent hydrocarbon group having 1 to 8 carbon atoms, ora group as defined for R³. Examples of the unsaturated hydrocarbon groupmay be those mentioned above. In particular, an allyl group and a vinylgroup are preferred. The saturated monovalent hydrocarbon group having 1to 8 carbon atoms is in particular an alkyl group, such as a methylgroup, an ethyl group, a propyl group, an isopropyl group, a butyl groupand an octyl group. Among these, a methyl group is preferred. R² isparticularly a methyl group, a hydrogen atom or a group as defined, forR³.

Examples of the (poly)oxyalkylene compound (B2) include the following:CH₂═CH—CH₂—O—(C₂H₄O)₈—HCH₂═CH—CH₂—O—(C₂H₄O)₁₆—HCH₂═CH—CH₂—O—(C₂H₄O)₁₂—(C₃H₆O)₂—HCH₂═CH—CH₂—O—(C₂H₄O)₆—CH₃CH₂═CH—CH₂—O—(C₃H₆O)₁₀—HCH₂═CH—CH₂—O—(C₂H₄O)₈—CH₂—CH═CH₂CH₂═CH—CH₂—O—(C₂H₄O)₁₆—CH₂—CH═CH₂CH₂═CH—CH₂—O—(C₂H₄O)₁₂—(C₃H₆O)₂—CH₂—CH═CH₂CH₂═CH—CH₂—O—(C₂H₄O)₆—CH₂—CH═CH₂

In particular, component (B) in the second embodiment is preferably the(poly)oxyalkylene compound (B1).

An amount of component (B) in the silicone adhesive compositionaccording to the second embodiment is preferably 0.27 to 3.3 parts bymass, more preferably 0.3 to 3 parts by mass, most preferably 0.6 to 1.8parts by mass, relative to 100 parts by mass of the additionreaction-curable silicone contained in the silicone adhesivecomposition. If the amount is less than the lower limit, the effect ofproviding an antistatic property is not sufficiently attained. If theamount is larger than the upper limit, an adhesion strength andcurability of the silicone adhesive composition may be lower and astrength of bond to a sheet substrate may be lower. The additionreaction-curable silicone is a conventional siloxane which is containedin silicone adhesive compositions, such as an organopolysiloxane havingan alkenyl group, an organohydrogenpolysiloxane and a silicone resin.The amount of component (B) is preferably such that a ratio of the totalnumber of the SiH groups in the silicone adhesive composition to thetotal number of the unsaturated hydrocarbon groups in component (B) andthe silicone adhesive composition is 1 to 20, more preferably 1 to 15,whereby component (B) is bonded strongly in the adhesive layer and,therefore, a residual adhesive is avoided as mentioned above.

(C) Ionic Liquid

The ioninc liquid is as described in the aforesaid first embodiment. Inthe second embodiment, an amount of component (C) is preferably 0.003 to1.5 parts by mass, more preferably 0.006 to 1.2 parts by mass, stillmore preferably 0.06 to 1.2 parts by mass, particularly 0.06 to 0.6 partby mass, relative to 100 parts by mass of the addition reaction-curablesilicone contained in the silicone adhesive composition. If the amountis less than the lower limit, the effect of providing an antistaticproperty is not sufficiently attained. If the amount is larger than theupper limit, an adhesion strength and curability of the siliconeadhesive composition may be lower and a strength of bond to a sheetsubstrate may be lower.

(e) Platinum Group Metal Catalyst

The silicone adhesive composition according to the second embodiment ischaracterized by comprising, as an addition reaction catalyst, aplatinum group metal catalyst which is not a complex with a compoundhaving an unsaturated hydrocarbon bond. The compound having anunsaturated hydrocarbon bond is particularly an olefinic compound or avinyl group-containing siloxane. The platinum group metal for formingthe complex includes platinum, palladium, rhodium and ruthenium.

Examples of the complex of the platinum group metal with the compoundhaving an unsaturated hydrocarbon bond include a reaction product ofchloroplatinic acid with an olefinic compound, a reaction product ofchloroplatinic acid with a vinyl group-containing siloxane, a complex ofplatinum with an olefinic compound, a complex of platinum with a vinylgroup-containing siloxane, a complex of rhodium with an olefin andchlorotris(triphenylphosphine)rhodium (Wilkinson's catalyst). These havegenerally been used as an addition reaction catalyst. However, whenthese catalysts are used in a silicone adhesive composition comprisingthe polyoxyalkylene compound having an unsaturated group (B), curabilityof the composition is not enough to cure the composition in a shorttime. Therefore, the catalysts need to be added in larger amounts thanusual. Further, a higher heating temperature and a longer heating timeare necessary for curing. It is unknown what causes the insufficientcurability. In the aforesaid complex, for example, a platinum atomcoordinates with an olefin or a vinyl group so that the platinum atom isstably present in a solution. The formation of the complex causes noproblem in usual silicone adhesive compositions which are additionreaction-curable. Meanwhile, when the aforesaid catalyst is used in thepresent silicone adhesive composition comprising the (poly)oxyalkylenecompound having an unsaturated group, curability of the composition islower. This is presumably because the olefin or the vinylgroup-containing siloxane is removed by heating and then the platinumatom is coordinated with the unsaturated group of the (poly)oxyalkylenecompound to inhibit early activation of the platinum atom.

Therefore, the silicone adhesive composition according to the secondembodiment is characterized by comprising a platinum group metalcatalyst which is not a complex with a compound having an unsaturatedhydrocarbon bond. Accordingly, the silicone adhesive composition cureswell by heating at a usual temperature for a short time, particularlyfor less than 5 minutes, more particularly for 30 seconds to 3 minutes.It is considered that this is because no platinum atom coordinates withan olefin or a vinyl group-containing siloxane in the platinum groupmetal catalyst which is not a complex with a compound having anunsaturated hydrocarbon bond, such as chloroplatinic acid, a solution ofchloroplatinic acid in an alcohol and an reaction product ofchloroplatinic acid with an alcohol, and, therefore, even if theplatinum atom is coordinated with the unsaturated group of the(poly)oxyalkylene compound upon the addition of the catalyst, theplatinum atom activates at an early stage.

In the second embodiment, any platinum group metal catalyst may be usedas long as it is not a complex with a compound having an unsaturatedhydrocarbon bond. The catalyst may be selected from those conventionallyused as an addition reaction catalyst, such as platinum group metalsthemselves such as platinum (including platinum black), rhodium andpalladium; platinum chloride, chloroplatinic acid and chloroplatinicacid salts such as H₂PtCl₄.kH₂O, H₂PtCl₆.kH₂O, NaHPtCl₆.kH₂O,KHPtCl₆.kH₂O, Na₂PtCl₆.kH₂O, K₂PtCl₄.kH₂O, PtCl₄.kH₂O, PtCl₂, andNa₂HPtCl₄.kH₂O wherein k is an integer of 0 to 6, preferably 0 or 6; analcohol denuatured-chloroplatinic acid; and a platinum group metal suchas platinum black and palladium supported on a carrier such as alumina,silica and carbon. Among these, platinum catalysts are preferred, andchloroplatinic acid, a solution of chloroplatinic acid in an alcohol anda reaction product of chloroplatinic acid with an alcohol are morepreferred.

Particularly, a solution of chloroplatinic acid in an alcohol and areaction product of chloroplatinic acid with an alcohol are preferred.These may be any conventional ones, such as one obtained by dissolvingchloroplatinic acid in an alcohol and one obtained by dissolvingchloroplatinic acid in an alcohol, followed by stirring at a temperatureof room temperature to 80 degrees C.

Preferred examples of the alcohol to be used in the solution ofchloroplatinic acid in an alcohol and in the reaction product ofchloroplatinic acid with an alcohol include alcohols having 1 to 8carbon atoms and boiling points of 200 degrees C. or lower. Alcoholshaving 3 to 7 carbon atoms are particularly preferred. If the boilingpoint is too low, a concentration of chloroplatinic acid may changeduring storage. If the boiling point is too high, the alcohol may remainin an adhesive after drying.

An amount of the catalyst may be a catalystic amount, i.e., an amounteffective in acclerating the addition reaction of components (a) and (B)with component (c). In particular, the amount is preferably such that anamount of a platinum group metal is 1 to 5,000 ppm, particularly 5 to1,000 ppm, relative to a total amount by mass of components (a), (B) and(b). If the amount is less than the lower limit, curability of thesilicone adhesive composition is lower and a degree of crosslinking in acured product of the composition is lower, so that a strength of bond toa sheet substrate may be lower. If the amount is larger than the upperlimit, the composition in a bath is usable only for a shorter period oftime.

Second Silicone Adhesive Composition Which is Addition Reaction-Curable

Components other than components (B), (C) and (e) contained in thesecond silicone adhesive composition which is addition reaction-curablemay be components contained in any conventional silicone adhesivecomposition which are addition reaction-curable, as mentioned above. Forexample, the addition curable silicone (A) may be the following (a) to(c) and, further, the following component (d) may be incorporated:

(a) a linear diorganopolysiloxane having two or more alkenyl groups inone molecule,

(b) an organopolysiloxane having R⁴ ₃SiO_(0.5) units and SiO₂ units in amole ratio of the R⁴ ₃SiO_(0.5) units to the SiO₂ units of 0.6 to 1.7,wherein R⁴ is a monovalent hydrocarbon group having 1 to 10 carbonatoms,

(c) an organopolysiloxane having two or mere SiH groups in one molecule,and

(d) optionally, a reaction inhibitor.

The details for the aforesaid components (a) to (d) are as explained inthe aforesaid first embodiment.

The second silicone adhesive composition according to the presentinvention may be prepared by adding components (B2), (C) and (e) to acommercially available silicone adhesive component which is additionreaction-curable. Examples of the commercially available siliconeadhesive component include KR-3700, KR-3701, KR-3704, X-40-3237 andKR-3706, ex Shin-Etsu Chemical Co. Ltd. When components (B2) and (C) areadded to a commercially available silicone adhesive component, it mayhappen that the ratio of the total number of SiH groups and the totalnumber of unsaturated hydrocarbon groups in the composition be outsidethe afore-mentioned range. In that case, the organohydrogenpolysiloxan(c) may be added to adjust the ratio.

The first and second silicone adhesive compositions according to thepresent invention may further comprise an organic solvent in order todecrease their viscosities in use in coating. The organic solvent isaromatic solvents such as toluene and sylene; aliphatic solvents such ashexane, octane and isoparaffins; ketone solvents such as methyl ethylketone and methyl isobutyl ketone; ester solvents such as ethyl acetateand isobutyl acetate; ether solvents such as diisopropyl ether and1,4-dioxane; and a mixture thereof.

In the present invention, ionic conductive materials other than lithiumsalts, and other organopolymeric antistatic agents may further be addedas long as the performances of the present silicone adhesive compositionare not obstructed.

The first and second silicone adhesive compositions according to thepresent invention may comprise other optional components in addition tothe aforesaid components. Examples of the optional component includeunreactive organopolysioxanes such as polydimethylsiloxsane andpolydimethyldiphenylsiloxane; antioxidants such as phenol, kinone,amine, phosphorus, phosphite, sulfur or thioether antioxidant; lightstabilizers such as a triazole or benzophenone light stabilizer; flameretardants such as a phosphate ester, halogen, phosphorus or antimonyflame retardant; and antistatic agents such as cationic activators,anionic activators and nonionic activators.

The first and second silicone adhesive compositions according to thepresent invention are prepared by mixing and dissolving the aforesaidcomponents with each other in any conventional manners. The mixing maybe carried out by mixing the components other than components (B) and(C) in advance and then adding components (B) and (C) to the mixture, orby mixing all of the components in one step. Particularly, the aforesaidcomponents (a) to (d) are first mixed with each other, to whichcomponents (B) and (C) and optionally component (c) are then added andmixed to obtain a homogeneous mixture. Then, an addition reactioncatalyst and optionally a solvent are added and mixed to obtain thepresent silicone adhesive composition.

The first or second silicone adhesive compositions may be applied on asubsrate in a sheet form and then cured in predetermined conditions toobtain an adhesive tape or film which has an adhesive layer. The sheetsubstrate to which the silicone adhesive composition is to be appliedmay be any conventional one. Examples of the substrate include plasticfilms such as polyesters, polytetrafluoroethylenes, polyimides,polyphenylene sulfides, polyamides, polyether ether ketones,polycarbonates, polystyrenes, polypropylenes, polyethylenes andpolyvinyl chlorides; mtal foil such as aluminum foil and cupper foil;paper such as traditional Japanese paper, synthetic paper andpolyethylene-laminated paper; cloths; glass fiber; and compositesubstrates obtained by laminating a plurality of the aforesaidsubstrates. The substrate may be subjected in advance, for example, toprimer treatment, corona treatment, etching treatment, plasma treatmentor plasma treatment, in order to improve a strength of bond by thesilicone adhesive layer.

The adhesive layer, i.e., cured product, obtained from the firstsilicone adhesive composition has a low surface resistivity and anexcellent antistatic property. The surface resistivity may be in anyrange as long as the adhesive layer is applicable to antistatic use. Thefirst silicone adhesive composition provides an adhesive layerpreferably having a surface resistivity of 1E+9 to less than 1E+13Ω/sq., i.e., 1×10⁹ to less than 1×10¹³ Ω/sq., more preferably 1E+9 to9.9E+12 Ω/sq., i.e., 1×10⁹ to 9.9×10¹² Ω/sq., still more preferably 1E+9to less than 1E+12 Ω/sq., i.e., 1×10⁹ to less than 1×10¹² Ω/sq.,particularly 1E+10 to 9.9E+11 Ω/sq., i.e., 1×10¹⁰ to 9.9×10¹¹ Ω/sq. Thesurface resistivity in the present invention is determined according toJIS K6911.

The second silicone adhesive composition according to the presentInvention is heated for a short time to provide an adhesive layer, i.e.,cured product, having a good antistatic property. The surfaceresistivity of the adhesive layer may be in any range as long as theadhesive layer is applicable to antistatic use. The second siliconeadhesive composition provides an adhesive layer preferably having asurface resistivity of 1E+9 to less than 1E+13 Ω/sq., i.e., 1×10⁹ toless than 1×10¹³ Ω/sq., more preferably 1E+9 to 9.9E+12 Ω/sq., i.e.,1×10⁹ to 9.9×10¹² Ω/sq., still more preferably 1E+9 to less than 1E+12Ω/sq., i.e., 1×10⁹ to less than 1×10¹² Ω/sq., particularly 1E+10 to9.9E+11 Ω/sq., i.e., 1×10¹⁰ to 9.9×10¹¹ Ω/sq. The surface resistivity inthe present invention is determined according to JIS K6911.

The first and second silicone adhesive compositions may be applied inany conventional manners. For example, use may be made of a commacoater, a lip coater, a roll coater, a die coater, a knife coater, ablade coater, a rod coater, a kiss coater, a gravure coater, screencoating, dip coating and cast coating. An amount of the composition tobe applied is preferably such that a thickness of the adhesive layerafter cured is 2 to 200 μm, particularly 3 to 100 μm. Curing conditionsfor the composition according to the first embodiment may be 80 to 150degrees C. for 30 seconds to 5 minutes, but are not limited thereto.Curing conditions for the composition according to the second embodimentare preferably 80 to 150 degrees C. for 30 seconds to less than 5minutes, particularly 80 to 140 degrees C. for 30 seconds to 3 minutes.

An adhesive tape may be prepared in any conventional manners, forexample, by applying the adhesive composition directly on a sheetsubstrate, followed by curing, as described above. Alternatively, it maybe prepared by a transfer method wherein the adhesive composition isapplied on a releasing film or paper-coated with a releasing agent, andcured and, then, the adhesive side is bonded to a sheet substrate.

The present adhesive tape has an excellent antistatic property. Further,no residual adhesive occurs when the adhesive tape is peeled from atape-stuck body. Therefore, the adhesive tape may be suitably used as anantistatic adhesive tape for various bodies. The tape-stuck body onwhich the present adhesive tape is to be applied is not particularlylimited, and may be metals such as stainless steel, copper and iron;these metals whose surface was subjected to plating or rustproofing;ceramics such as glasses and ceramic wares; resins such aspolytetrafluoroethylenes, polyimides, epoxy resins and novolac resins;and composites thereof.

EXAMPLES

The present invention will be explained in more detail by reference tothe Examples and the Comparative Examples, but shall not be limitedthereto.

Part I: First Embodiment

The Examples and the Comparative Examples for the first embodiment aredescribed in Part I. Components used in the Examples and the ComparativeExamples are as follows. The viscosity was hereinafter determined at 25degrees C. with a Brookfield rotary viscometer of the BM type.

(A) Addition Reaction-Curable Silicone

-   -   Polysiloxane (a1): vinyl group-containing polydimethylsiloxane        with the molecular chain terminals each capped with a        dimethylvinylsilyl (SiMe₂Vi) group, having a viscosity of 27000        mPa·s in a 30% solution in toluene and a vinyl group content of        0.075 mole %    -   Polysiloxane (a2): vinyl group-containing polydimethylsiloxane        with the molecular chain terminals each capped with a        dimethylvinylsilyl (SiMe₂Vi) group, having a viscosity of 27000        mPa·s in a 30% solution in toluene and a vinyl group content of        0.15 mole %    -   Polysiloxane (b): a 60% solution of polysilosane composed of        Me₃SiO_(0.5) units and SiO₂ units (Me₃SiO_(0.5) units/SiO₂        units=0.82), in toluene    -   Polysiloxane (c1): organohydrogenpolysiloxane represented by the        following formula:

-   -   Polysiloxane (c2): organohydrogenpolysiloxane represented by the        following formula:

Component (B1): polyoxyalkylene represented by the following formula:

wherein m and n are a combination of (m,n)=(2,0), (8,0), (12,0), (18,0),(0,8) or (6,2). The combination of m and n in component (B1) used in theExamples and the Comparative Examples is as shown in the followingTables.Component (C):

-   -   Ionic liquid A: trimethylpropylammonium        bis(trifluoromethanesulfonyl)imide    -   Ionic liquid B: butyltrimethylammonium bis(trifluoromethyl        sulfonyl)imide    -   Ionic liquid C: ethyldimethylpropylammonium        bis(trifluoromethylsulfonyl)imide        Comparative polyoxyalkylene (1): polyoxyalkylene represented by        the following formula:

wherein m and n are a combination of (m,n)=(22,0) or (0,12). Thecombination of m and n in the comparative polyoxyalkylene used in theComparative Examples is as shown in the following Tables.

Comparative polyoxyalkylene (2): polyoxyalkylene having one unsaturatedhydrocarbon group and one polyoxyalkylene residue in one molecule, andrepresented by the following formula (a) or (b):CH₂═CH—CH₂—O—(C₂H₄O)₄—H  (a)CH₂═CH—CH₂—O—(C₂H₄O)₈—CH₃  (b)

Comparative polyoxyalkylene (3): polyoxyalkylene having onepolyoxyalkylene residue and two unsaturated hydrocarbon groups in onemolecule, and represented by the following formula (c) or (d):CH₂═CH—CH₂—O—(C₂H₄O)₈—CH₂—CH═CH₂  (c)CH₂═CH—CH₂—O—(C₂H₄O)₁₆—CH₂—CH═CH₂  (d)

Comparative polyoxyalkylene (4): polyoxyalkylene having twopolyoxyalkylene residues and no unsaturated hydrocarbon group in onemolecule, and represented by the following formula (e):

Comparative lithium salt: lithium bis(trifluoromethanesulfonyl)imide

Preparation Example I-1

Preparation of Silicone Adhesive Composition (I-α)

Forty parts by mass of polysiloxane (a1), 83.3 parts by mass ofpolysiloxane (b), 0.4 part by mass of polysiloxane (c1) and 33.3 partsby mass of toluene were mixed to obtain a solution, to which 0.2 part bymass of 1-ethynylcyclohexanol was added and mixed to obtain a mixturehaving a siloxane content of approximately 60% by mass at a ratio of thenumber of the SiH groups in component (c1) to the number of the alkenylgroups in component (a2) of 15. To 100 parts by mass of the mixture, the(poly)oxyalkylene shown in the following Tables, ionic liquid (C) or thelithium salt shown in the Tables, and polysiloxane (c2) were added inthe amounts in part by mass shown in the Tables, and then stirred toobtain a homogeneous mixture. To 100 parts by mass of the mixture, 50parts by mass of toluene were added, and then mixed to prepare a mixturehaving a siloxane content of approximately 40% by mass. A reactionproduct (complex) of chloroplatinic acid with a vinyl group-containingsiloxane was added so that the mass of platinum atoms was 250 ppmrelative to a total mass of components (a) and (b), and then stirredenough to obtain a silicone adhesive composition (I-α). It is noted thatthe amount of polysiloxane (c2) was such that a ratio of the number ofthe SiH groups in polysiloxane (c2) to the number of the alkenyl groupsin component (B1) or in the comparative polyoxyalkylene was 1.

Preparation of Silicone Adhesive Composition (I-β)

Ninety five parts by mass of polysiloxane (a2), 8.3 parts by mass ofpolysiloxane (b), 0.6 part by mass of polysiloxane (c1) and 33.3 partsby mass of toluene were mixed to obtain a solution, to which 0.2 part bymass of 1-ethynylcyclohexanol was added to obtain a mixture having asiloxane content of approximately 60% by mass at a ratio of the numberof the SiH groups in component (c1) to the number of the alkenyl groupsin component (a2) of 5. To 100 parts by mass of the mixture, the(poly)oxylalkylene shown in the following Tables, ionic liquid (C) orthe lithium salt shown in the Tables, and polysiloxane (c2) were addedin the amounts in part by mass shown in the Tables, and then stirred toobtain a homogeneous mixture. To 100 parts by mass of the mixture, 50parts by mass of toluene were added, and then mixed to prepare a mixturehaving a siloxane content of approximately 40% by mass. A reactionproduct (complex) of chloroplatinic acid with a vinyl group-containingsiloxane was added so that the mass of platinum atoms was 250 ppmrelative to a total mass of components (a) and (b), and then stirredenough to obtain a silicone adhesive composition (I-β). It is noted thatthe amount of polysiloxane (c2) was such that a ratio of the number ofthe SiH groups in polysiloxane (c2) to the number of the alkenyl groupsin component (B1) or in the comparative polyoxyalkylene was 1.

The silicone adhesive compositions obtained above were subjected to thefollowing tests.

Curability

The silicone adhesive composition was applied on a polyimide film havinga dimension of 110 mm×110 mm and a thickness of 25 μm with an applicatorso as to provide a coating having a thickness of 30 μm and, then, heatedat 130 degrees C. for 5 minutes to be cured, to thereby prepare anadhesive sheet. The adhesive sheet was put on a surface of stainlesssteel of SUS304 polished with grade #280 sandpaper and, then, pressed byone cycle of going and returning of a 2 kg roller. Then, the adhesivesheet was peeled from the stainless steel surface to evaluatecurability. In a case where no adhesive remained on the stainless steelsurface, curing proceeded sufficiently and no adhesive transferred tothe substrate. Curability was evaluated as G. Meanwhile in a case wheresome adhesive remained on the stainless steel surface, curing did notsufficiently proceed and some adhesive transferred to the substrate.Curability was evaluated as NG.

Strength of Bond to a Sheet Substrate (Hereinafter Referred to as BondStrength)

The antistatic silicone adhesive composition was applied on a polyimidefilm having a dimension of 110 mm×110 mm and a thickness of 25 μm withan applicator so as to provide a coating having a thickness of 30 μmand, then, heated at 130 degrees C. for 5 minutes to be cured, tothereby prepare an adhesive sheet. The adhesive sheet was put on asurface of stainless steel of SUS304 polished with grade #280 sandpaperand, then, pressed by one cycle of going and returning of a 2 kg roller.Then, the adhesive sheet was peeled from the stainless steel surface toevaluate a strength of bond to the sheet substrate (polyimide film). Ina case where the adhesive separated from the sheet substrate, or peeledfrom the sheet substrate and transferred wholly to the stainless steelsurface, the bond strength was evaluated as NG. Meanwhile in a casewhere the adhesive did not separate from the sheet substrate and noadhesive remained on the stainless steel surface, the bond strength wasevaluated as G. It is noted that the composition which was evaluated asNG in the aforesaid curability test is naturally NG also in this testand, therefore, was not subjected to this test. This is indicated as “−”in the Tables.

Surface Resistivity

The silicone adhesive composition was applied on a polyimide film havinga dimension of 110 mm×110 mm and a thickness of 25 μm with an applicatorso as to provide a coating having a thickness of 30 μm and, then, heatedat 130 degrees C. for 5 minutes to be cured, to thereby prepare anadhesive sheet. The surface resistivity of the adhesive sheet wasdetermined according to JIS-K6911 using Hiresta UP MCT-UP450, ex DiaInstruments Co., Ltd., at an applied voltage of 500V. The determinationwas carried out two or more times. In the Tables, a surface resistivityin the range of 1E+9 to 5E+9 Ω/sq., i.e., 1×10⁹ to 5×10⁹ Ω/sq. isindicated as a former half of the order of 10⁹. A surface resistivity inthe range of more than 5E+9 to 9.9E+9 Ω/sq., i.e., more than 5×10⁹ to9.9×10⁹ Ω/sq. is indicated as a latter half of the order of 10⁹.Similarly, the following surface resistivities are indicated as follows:1E+10 to 5E+10 Ω/sq., i.e., 1×10¹⁰ to 5×10¹⁰ Ω/sq.: former half of theorder of 10¹⁰;

more than 5E+10 to 9.9E+10 Ω/sq., i.e., more than 5×10¹⁰ to 9.9×10¹⁰Ω/sq.: latter half of the order of 10¹⁰;

1E+11 to 5E+11 Ω/sq., i.e., 1×10¹¹ to 5×10¹¹ Ω/sq.: former half of theorder of 10¹¹;

more than 5E+11 to 9.9E+11 Ω/sq., i.e., more than 5×10¹¹ to 9.9×10¹¹Ω/sq.: latter half of the order of 10¹¹;

1E+12 to 5E+12 Ω/sq., i.e., 1×10¹² to 5×10¹² Ω/sq.: former half of theorder of 10¹²;

more than 5E+12 to 9.9E+12 Ω/sq., i.e., more than 5×10¹² to 9.9×10¹²Ω/sq.: latter half of the order of 10¹²;

1E+13 to 5E+13 Ω/sq., i.e., 1×10¹³ to 5×10¹³ Ω/sq.: former half of theorder of 10¹³;

more than 5E+13 to 9.9E+13 Ω/sq., i.e., more them 5×10¹³ to 9.9×10¹³Ω/sq.: latter half of the order of 10¹³;

1E+14 to 5E+14 Ω/sq., i.e., 1×10¹⁴ to 5×10¹⁴ Ω/sq.: former half of theorder of 10¹⁴;

more than 5E+14 to 9.9E+14 Ω/sq., i.e., more than 5×10¹⁴ to 9.9×10¹⁴Ω/sq.: latter half of the order of 10¹⁴; and

1E+15 Ω/sq. or more, i.e., 1×10¹⁵ Ω/sq. or more: 10¹⁵ or more.

The evaluation results of the various silicone adhesive compositions(I-α) comprising the various types of oxyalkylene compounds and ionicliquids in the various amounts are as shown in Tables 1(I) to 14(I). Theevaluation results of the various silicone adhesive compositions (I-β)comprising the various types of oxyalkylene compounds and ionic liquidsin the various amounts are as shown in Tables 15(I) to 28(I). Further,the evaluation results of the various silicone adhesive compositions(I-α) and the various silicone adhesive compositions (I-β) whichcomprised the polyoxyalkylene compound represented by the formula (e)having no unsaturated hydrocarbon group in place of component (B1) areas shown in Tables 29(I) to 30(I).

Silicone Adhesive Composition I-α

In Examples 1(I) to 4(I) and Comparative Examples 1(I) and 2(I),polyoxyalkylene compound (B1) with m=2 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 1(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 1(I) Component (B1) Component (C) Amount, Amount, Component (c2)Evaluation results Comparative part by part by Amount, Surface BondExample Example m n mass Type mass part by mass Curability resistivitystrength Example 1 2 0 0.5 A 0.5 0.25 G Latter half of the G order of10¹² Example 2 1 0.5 G Latter half of the G order of 10¹⁰ Example 3 31.49 G Former half of the G order of 10¹⁰ Example 4 5 2.48 G Former halfof the G order of 10¹⁰ Comp. 0.4 0.1 G Former half of the G Example 1order of 10¹³ Comp. 6 2.97 NG Former half of the — Example 2 order of10¹⁰Silicone Adhesive Composition I-α

In Examples 5(I) to 8(I) and Comparative Examples 3(I) and 4(I),polyoxyalkylene compound (B1) with m=8 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 2(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 2(I) Component (B1) Component (C) Amount, Amount, Component (c2)Evaluation results Comparative part by part by Amount, Surface BondExample Example m n mass Type mass part by mass Curability resistivitystrength Example 5 8 0 0.5 A 0.5 0.12 G Latter half of the G order of10¹² Example 6 1 0.25 G Former half of the G order of 10¹¹ Example 7 30.74 G Latter half of the G order of 10¹⁰ Example 8 5 1.23 G Latter halfof the G order of 10¹⁰ Comp. 0.4 0.1 G Former half of the G Example 3order of 10¹³ Comp. 6 1.47 NG Former half of the — Example 4 order of10¹⁰Silicone Adhesive Composition I-α

In Examples 9(I) to 12(I) and Comparative Examples 5(I) and 6(I),polyoxyalkylene compound (B1) with m=12 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 3(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 3(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Example 9 12 0 0.5 A 0.5 0.08 G Latter half of the order of10¹² G Example 10 1 0.16 G Former half of the order of 10¹¹ G Example 113 0.49 G Latter half of the order of 10¹⁰ G Example 12 5 0.81 G Latterhalf of the order of 10¹⁰ G Comp. 0.4 0.07 G Former half of the order of10¹³ G Example 5 Comp. 6 0.98 NG Former half of the order of 10¹⁰ —Example 6Silicone Adhesive Composition I-α

In Examples 13(I) to 16(I) and Comparative Examples 7(I) and 8(I),polyoxyalkylene compound (B1) with m=18 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 4(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 4(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Example 13 18 0 0.5 A 0.5 0.07 G Latter half of the order of10¹² G Example 14 1 0.13 G Latter half of the order of 10¹¹ G Example 153 0.4 G Former half of the order of 10¹¹ G Example 16 5 0.67 G Formerhalf of the order of 10¹¹ G Comp. 0.4 0.05 G Former half of the order of10¹³ G Example 7 Comp. 6 0.8 NG Former half of the order of 10¹¹ —Example 8Silicone Adhesive Composition I-α

In Examples 17(I) to 20(I) and Comparative Examples 9(I) and 10(I),polyoxyalkylene compound (B1) with m=0 and n=8 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. In Examples21(I) to 23(I), polyoxyalkylene compound (B1) with m=6 and n=2 andioninc liquid A were used in the various amounts of the polyoxyalkylenecompound. The results are as shown in Table 5(I). The term “(I)” in theExample and Comparative Example numbers is omitted in this Table.

TABLE 5(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Ex. 17 0 8 0.5 A 0.5 0.1 G Latter half of the order of 10¹² GEx. 18 1 0.19 G Latter half of the order of 10¹¹ G Ex. 19 3 0.58 GFormer half of the order of 10¹¹ G Ex. 20 5 0.97 G Former half of theorder of 10¹¹ G Comp. 0.4 0.08 G Former half of the order of 10¹³ G Ex.9 Comp. 6 1.16 NG Former half of the order of 10¹¹ — Ex. 10 Ex. 21 6 20.5 A 0.5 0.09 G Latter half of the order of 10¹¹ G Ex. 22 1 0.18 GLatter half of the order of 10¹¹ G Ex. 23 3 0.53 G Former half of theorder of 10¹¹ GSilicone Adhesive Composition I-α

In Examples 24(I) to 27(I) and Comparative Examples 11(I) and 12(I),polyoxyalkylene compound (B1) with m=2 and n=0 and ioninc liquid B wereused in the various amounts of the polyoxyalkylene compound. In Examples28(I) to 31(I) and Comparative Examples 13(I) and 14(I), polyoxyalkylenecompound (B1) with m=8 and n=0 and ioninc liquid B were used in thevarious amounts of the polyoxyalkylene compound. The results are asshown in Table 6(I). The term “(I)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 6(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Ex. 24 2 0 0.5 B 0.5 0.25 G Latter half of the order of 10¹² GEx. 25 1 0.5 G Latter half of the order of 10¹⁰ G Ex. 26 3 1.49 G Formerhalf of the order of 10¹⁰ G Ex. 27 5 2.48 G Former half of the order of10¹⁰ G Comp. 0.4 0.1 G Former half of the order of 10¹² G Ex. 11 Comp. 62.97 NG Former half of the order of 10¹⁰ — Ex. 12 Ex. 28 8 0 0.5 A 0.50.08 G Latter half of the order of 10¹¹ G Ex. 29 1 0.16 G Former half ofthe order of 10¹¹ G Ex. 30 3 0.49 G Latter half of the order of 10¹⁰ GEx. 31 5 0.81 G Latter half of the order of 10¹⁰ G Comp. 0.4 0.07 GFormer half of the order of 10¹³ G Ex. 13 Comp. 6 0.98 NG Former half ofthe order of 10¹⁰ — Ex. 14Silicone Adhesive Composition I-α

In Examples 32(I) to 35(I) and Comparative Examples 15(I) and 16(I),polyoxyalkylene compound (B1) with m=2 and n=0 and ioninc liquid C wereused in the various amounts of the polyoxyalkylene compound. In Examples36(I) to 39(I) and Comparative Examples 17(I) and 18(I), polyoxyalkylenecompound (B1) with m=8 and n=0 and ioninc liquid C were used in thevarious amounts of the polyoxyalkylene compound. The results are asshown in Table 7(I). The term “(I)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 7(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Ex. 32 2 0 0.5 C 0.5 0.25 G Latter half of the order of 10¹¹ GEx. 33 1 0.5 G Latter half of the order of 10¹⁰ G Ex. 34 3 1.49 G Formerhalf of the order of 10¹⁰ G Ex. 35 5 2.48 G Former half of the order of10¹⁰ G Comp. 0.4 0.2 G Former half of the order of 10¹² G Ex. 15 Comp. 62.97 NG Former half of the order of 10¹⁰ — Ex. 16 Ex. 36 8 0 0.5 A 0.50.08 G Latter half of the order of 10¹¹ G Ex. 37 1 0.16 G Former half ofthe order of 10¹¹ G Ex. 38 3 0.49 G Latter half of the order of 10¹⁰ GEx. 39 5 0.81 G Latter half of the order of 10¹⁰ G Comp. 0.4 0.07 GFormer half of the order of 10¹² G Ex. 17 Comp. 6 0.98 NG Former half ofthe order of 10¹⁰ — Ex. 18Silicone Adhesive Composition I-α

In Examples 40(I) to 47(I), ioninc liquid A was used in an amount of0.01 part by mass. In Examples 48(I) to 55(I), ioninc liquid A was usedin an amount of 2 parts by mass. The results are as shown in Table 8(I).The term “(I)” in the Example numbers is omitted in this Table.

TABLE 8(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results part by part by part by Bond Example m n massType mass mass Curability Surface resistivity strength Ex. 40 2 0 0.5 A0.01 0.25 G Latter half of the order of 10¹¹ G Ex. 41 1 A 0.5 G Latterhalf of the order of 10¹⁰ G Ex. 42 3 A 1.49 G Former half of the orderof 10¹⁰ G Ex. 43 5 A 2.48 G Former half of the order of 10¹⁰ G Ex. 44 80 0.5 A 0.08 G Latter half of the order of 10¹¹ G Ex. 45 1 A 0.16 GFormer half of the order of 10¹¹ G Ex. 46 3 A 0.49 G Latter half of theorder of 10¹⁰ G Ex. 47 5 A 0.81 G Latter half of the order of 10¹⁰ G Ex.48 2 0 0.5 A 2 0.25 G Latter half of the order of 10¹¹ G Ex. 49 1 A 0.5G Latter half of the order of 10¹⁰ G Ex. 50 3 A 1.49 G Former half ofthe order of 10¹⁰ G Ex. 51 5 A 2.48 G Former half of the order of 10¹⁰ GEx. 52 8 0 0.5 A 0.08 G Latter half of the order of 10¹¹ G Ex. 53 1 A0.16 G Former half of the order of 10¹¹ G Ex. 54 3 A 0.49 G Latter halfof the order of 10¹⁰ G Ex. 55 5 A 0.81 G Latter half of the order of10¹⁰ GSilicone Adhesive Composition I-α

In Comparative Examples 19(I) to 27(I), ioninc liquid A was used in anamount of 3 parts by mass. In Comparative Examples 28(I) to 30(I), noioninc liquid was used. The results are as shown in Table 9(I). The term“(I)” in the Comparative Example numbers is omitted in this Table.

TABLE 9(I) Component (B1) Component (C) Component (c2) amount, amount,Amount, Evaluation results Comparative part by part by part by BondExample m n mass Type mass mass Curability Surface resistivity strengthComp. Ex. 19 2 0 0.4 A 3 0.2 NG Former half of the order of 10¹² — Comp.Ex. 20 0 0.5 0.25 NG Former half of the order of 10¹² — Comp. Ex. 21 0 10.5 NG Latter half of the order of 10¹¹ — Comp. Ex. 22 0 3 1.49 NGLatter half of the order of 10¹⁰ — Comp. Ex. 23 8 0 0.4 0.03 NG Formerhalf of the order of 10¹⁰ — Comp. Ex. 24 0 0.5 0.08 NG Former half ofthe order of 10¹² — Comp. Ex. 25 0 1 0.16 NG Latter half of the order of10¹¹ — Comp. Ex. 26 0 3 0.49 NG Former half of the order of 10¹¹ — Comp.Ex. 27 0 5 0.81 NG Latter half of the order of 10¹⁰ — Comp. Ex. 28 2 00.5 — 0.25 G Former half of the order of 10¹⁴ G Comp. Ex. 29 0 5 2.48 GFormer half of the order of 10¹⁴ G Comp. Ex. 30 0 6 2.97 G Former halfof the order of 10¹⁴ NGSilicone Adhesive Composition I-α

In Comparative Examples 31(I) to 34(I), no polyoxyalkylene compound wasused. In Comparative Example 35(I), neither polyoxyalkylene compound norioninc liquid was used. The results are as shown in Table 10(I). Theterm “(I)” in the Comparative Example numbers is omitted in this Table.

TABLE 10(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample m n mass type mass mass Curability Surface resistivity strengthComp. Ex. 31 — A 0.5 — G Former half of the order of 10¹³ G Comp. Ex. 321 G Former half of the order of 10¹³ G Comp. Ex. 33 3 G Former half ofthe order of 10¹³ G Comp. Ex. 34 5 G Former half of the order of 10¹³ GComp. Ex. 35 — — G 10¹⁵ or more GSilicone Adhesive Composition I-α

In Comparative Examples 36(I) to 46(I), the lithium salt was substitutedfor component (C). The results are as shown in Table 11(I). The term“(I)” in the Comparative Example numbers is omitted in this Table.

TABLE 11(I) Lithium Component (B1) salt Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample m n mass mass mass Curability Surface resistivity strength Comp.Ex. 36 2 0 0.4 0.5 0.1 G Former half of the order of 10¹¹ NG Comp. Ex.37 0.5 0.5 0.25 G Latter half of the order of 10¹⁰ NG Comp. Ex. 38 0.50.05 0.5 G Latter half of the order of 10⁹ NG Comp. Ex. 39 0.5 0.01 0.5G Latter half of the order of 10⁹ NG Comp. Ex. 40 1 0.5 0.5 G Latterhalf of the order of 10⁹ NG Comp. Ex. 41 3 0.5 1.49 G Former half of theorder of 10⁹ NG Comp. Ex. 42 5 0.5 2.48 G Former half of the order of10⁹ NG Comp. Ex. 43 8 0 0.5 0.5 0.08 G Latter half of the order of 10¹⁰NG Comp. Ex. 44 1 0.16 G Former half of the order of 10¹⁰ NG Comp. Ex.45 3 0.81 G Latter half of the order of 10⁹ NG Comp. Ex. 46 0.4 0.49 GFormer half of the order of 10¹¹ NGSilicone Adhesive Composition I-α

In Comparative Examples 47(I) and 48(I), comparative polyoxyalkylenecompound (1) with m=0 and n=12 was used. In Comparative Examples 49(I)and 50(I), comparative polyoxyalkylene compound (1) with m=22 and n=0was used. The results are as shown in Table 12(I). The term “(I)” in theComparative Example numbers is omitted in this Table.

TABLE 12(I) Polyoxyalkylene compound (1) Component (C) Component (c2)Amount, Amount, Amount, Evaluation results Comparative part by part bypart by Bond Example m n mass Type mass mass Curability Surfaceresistivity strength Comp. Ex. 47 0 12 1 A 0.5 0.16 G Former half of theorder of 10¹³ NG Comp. Ex. 48 3 0.49 NG Former half of the order of 10¹³— Comp. Ex. 49 22 0 1 0.12 G Former half of the order of 10¹² NG Comp.Ex. 50 3 0.37 NG Latter half of the order of 10¹¹ —Silicone Adhesive Composition I-α

In Comparative Examples 51(I) to 56(I), comparative polyoxyalkylenecompound (a) or (b) having one unsaturated hydrocarbon group and onepolyoxyalkylene residue in one molecule was used. The results are asshown in Table 13(I). The term “(I)” in the Comparative Example numbersis omitted in this Table.

TABLE 13(I) Polyoxyalkylene compound Component (C) Component (c2)Amount, Amount, Amount, Evaluation results Comparative part by part bypart by Bond Example Type mass Type mass mass Curability Surfaceresistivity strength Comp. Ex. 51 (a) 0.5 A 0.5 0.14 G Latter half ofthe order of 10¹² NG Comp. Ex. 52 1 0.27 G Former half of the order of10⁹ NG Comp. Ex. 53 3 0.82 G Former half of the order of 10⁹ NG Comp.Ex. 54 (b) 0.5 0.13 G Latter half of the order of 10¹² NG Comp. Ex. 55 10.26 G Former half of the order of 10⁹ NG Comp. Ex. 56 3 0.78 G Formerhalf of the order of 10⁹ NGSilicone Adhesive Composition I-α

In Comparative Examples 57(I) to 62(I), comparative polyoxyalkylenecompound (c) or (d) having one polyoxyalkylene residue in one moleculewas used. The results are as shown in Table 14(I). The term “(I)” in theComparative Example numbers is omitted in this Table.

TABLE 14(I) Polyoxyalkylene compound Component (C) Amount, Amount,Evaluation results part by part by Component (c2) Bond Type mass Typemass Type Curability Surface resistivity strength Comp. Ex. 57 (c) 0.5 A0.5 0.25 G Latter half of the order of 10¹³ G Comp. Ex. 58 1 0.49 GFormer half of the order of 10¹³ G Comp. Ex. 59 5 2.47 NG Latter half ofthe order of 10¹² — Comp. Ex. 60 (d) 0.5 0.13 G Latter half of the orderof 10¹³ G Comp. Ex. 61 1 0.27 G Former half of the order of 10¹³ G Comp.Ex. 62 5 1.34 NG Latter half of the order of 10¹² —Silicone Adhesive Composition I-β

In Examples 56(I) to 59(I) and Comparative Examples 63(I) and 64(I),polyoxyalkylene compound (B1) with m=2 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 15(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 15(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Example 56 2 0 0.5 A 0.5 0.25 G Latter half of the order of10¹² G Example 57 1 0.5 G Latter half of the order of 10¹⁰ G Example 583 1.49 G Former half of the order of 10¹⁰ G Example 59 5 2.48 G Formerhalf of the order of I0¹⁰ G Comp. 0.4 0.1 G Former half of the order of10¹³ G Example 63 Comp. 6 2.97 NG Former half of the order of 10¹⁰ —Example 64Silicone Adhesive Composition I-β

In Examples 60(I) to 63(I) and Comparative Examples 65(I) and 66(I),polyoxyalkylene compound (B1) with m=8 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 16(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 16(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comp. part by part by part by Bond ExampleExample m n mass type mass mass Curability Surface resistivity strengthExample 60 8 0 0.5 A 0.5 0.12 G Former half of the order of 10¹² GExample 61 1 0.25 G Former half of the order of 10¹¹ G Example 62 3 0.74G Latter half of the order of 10¹⁰ G Example 63 5 1.23 G Latter half ofthe order of 10¹⁰ G Comp. 0.4 0.1 G Former half of the order of 10¹³ GExample 65 Comp. 6 1.47 NG Former half of the order of 10¹⁰ — Example 66Silicone Adhesive Composition I-β

In Examples 64(I) to 67(I) and Comparative Examples 67(I) and 68(I),polyoxyalkylene compound (B1) with m=12 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 17(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 17(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comp. part by part by part by Bond ExampleExample m n mass Type mass mass Curability Surface resistivity strengthExample 64 12 0 0.5 A 0.5 0.08 G Former half of the order of 10¹² GExample 65 1 0.16 G Former half of the order of 10¹¹ G Example 66 3 0.49G Latter half of the order of 10¹⁰ G Example 67 5 0.81 G Latter half ofthe order of 10¹⁰ G Comp. 0.4 0.07 G Former half of the order of 10¹³ GExample 67 Comp. 6 0.98 NG Former half of the order of 10¹⁰ — Example 68Silicone Adhesive Composition I-β

In Examples 68(I) to 71(I) and Comparative Examples 69(I) and 70(I),polyoxyalkylene compound (B1) with m=18 and n=0 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. The resultsare as shown in Table 18(I). The term “(I)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 18(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Example 68 18 0 0.5 A 0.5 0.07 G Former half of the order of10¹² G Example 69 1 0.13 G Latter half of the order of 10¹¹ G Example 703 0.4 G Former half of the order of 10¹¹ G Example 71 5 0.67 G Formerhalf of the order of 10¹¹ G Comp. 0.4 0.05 G Former half of the order of10¹³ G Example 69 Comp. 6 0.8 NG Former half of the order of 10¹¹ —Example 70Silicone Adhesive Composition I-β

In Examples 72(I) to 75(I) and Comparative Examples 71(I) and 72(I),polyoxyalkylene compound (B1) with m=0 and n=8 and ioninc liquid A wereused in the various amounts of the polyoxyalkylene compound. In Examples76(I) to 78(I), polyoxyalkylene compound (B1) with m=6 and n=2 andioninc liquid A were used in the various amounts of the polyoxyalkylenecompound. The results are as shown in Table 19(I). The term “(I)” in theExample and Comparative Example numbers is omitted in this Table.

TABLE 19(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Ex. 72 0 8 0.5 A 0.5 0.1 G Latter half of the order of 10¹¹ GEx. 73 1 0.19 G Latter half of the order of 10¹¹ G Ex. 74 3 0.58 GFormer half of the order of 10¹¹ G Ex. 75 5 0.97 G Former half of theorder of 10¹¹ G Comp. 0.4 0.08 G Former half of the order of 10¹² G Ex.71 Comp. 6 1.16 NG Former half of the order of 10¹¹ — Ex. 72 Ex. 76 6 20.5 A 0.5 0.09 G Latter half of the order of 10¹¹ G Ex. 77 1 0.18 GLatter half of the order of 10¹¹ G Ex. 78 3 0.53 G Former half of theorder of 10¹¹ GSilicone Adhesive Composition I-β

In Examples 79(I) to 82(I) and Comparative Examples 73(I) and 74(I),polyoxyalkylene compound (B1) with m=2 and n=0 and ioninc liquid B wereused in the various amounts of the polyoxyalkylene compound. In Examples83(I) to 86(I) and Comparative Examples 75(I) and 76(I), polyoxyalkylenecompound (B1) with m=8 and n=0 and ioninc liquid B were used in thevarious amounts of the polyoxyalkylene compound. The results are asshown in Table 20(I). The term “(I)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 20(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Ex. 79 2 0 0.5 B 0.5 0.25 G Latter half of the order of 10¹² GEx. 80 1 0.5 G Latter half of the order of 10¹⁰ G Ex. 81 3 1.43 G Formerhalf of the order of 10¹⁰ G Ex. 82 5 2.48 G Former half of the order of10¹⁰ G Comp. 0.4 0.1 G Former half of the order of 10¹² G Ex. 73 Comp. 62.97 NG Former half of the order of 10¹⁰ — Ex. 74 Ex. 83 8 0 0.5 0.08 GLatter half of the order of 10¹¹ G Ex. 84 1 0.16 G Former half of theorder of 10¹¹ G Ex. 85 3 0.49 G Latter half of the order of 10¹¹ G Ex.86 5 0.81 G Latter half of the order of 10¹⁰ G Comp. 0.4 0.07 G Formerhalf of the order of 10¹³ G Ex. 75 Comp. 6 0.98 NG Former half of theorder of 10¹⁰ — Ex. 76Silicone Adhesive Composition I-β

In Examples 87(I) to 90(I) and Comparative Examples 77(I) and 78(I),polyoxyalkylene compound (B1) with m=2 and n=0 and ioninc liquid C wereused in the various amounts of the polyoxyalkylene compound. In Examples91(I) to 94(I) and Comparative Examples 79(I) and 80(I), polyoxyalkylenecompound (B1) with m=8 and n=0 and ioninc liquid C were used in thevarious amounts of the polyoxyalkylene compound. The results are asshown in Table 21(I). The term “(I)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 21(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample Example m n mass Type mass mass Curability Surface resistivitystrength Ex. 87 2 0 0.5 C 0.5 0.25 G Latter half of the order of 10¹² GEx. 88 1 0.5 G Latter half of the order of 10¹⁰ G Ex. 89 3 1.49 G Formerhalf of the order of 10¹⁰ G Ex. 90 5 2.48 G Former half of the order of10¹⁰ G Comp. 0.4 0.2 G Former half of the order of 10¹² G Ex. 77 Comp. 62.97 NG Former half of the order of 10¹⁰ — Ex. 78 Ex. 91 8 0 0.5 0.08 GLatter half of the order of 10¹¹ G Ex. 92 1 0.16 G Former half of theorder of 10¹¹ G Ex. 93 3 0.49 G Latter half of the order of 10¹⁰ G Ex.94 5 0.81 G Latter half of the order of 10¹⁰ G Comp. 0.4 0.07 G Formerhalf of the order of 10¹³ G Ex. 79 Comp. 6 0.98 NG Former half of theorder of 10¹⁰ — Ex. 80Silicone Adhesive Composition I-α

In Examples 95(I) to 102(I), ioninc liquid A was used in an amount of0.01 part by mass. In Examples 103(I) to 110(I), ioninc liquid A wasused in an amount of 2 parts by mass. The results are as shown in Table22(I). The term “(I)” in the Example numbers is omitted in this Table.

TABLE 22(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results part by part by part by Bond Example m n massType mass mass Curability Surface resistivity strength Ex. 95 2 0 0.5 A0.01 0.25 G Latter half of the order of 10¹¹ G Ex. 96 1 A 0.5 G Latterhalf of the order of 10¹⁰ G Ex. 97 3 A 1.49 G Former half of the orderof 10¹⁰ G Ex. 98 5 A 2.48 G Former half of the order of 10¹⁰ G Ex. 99 80 0.5 A 0.08 G Latter half of the order of 10¹¹ G Ex. 100 1 A 0.16 GFormer half of the order of 10¹¹ G Ex. 101 3 A 0.49 G Latter half of theorder of 10¹⁰ G Ex. 102 5 A 0.81 G Latter half of the order of 10¹⁰ GEx. 103 2 0 0.5 A 2 0.25 G Latter half of the order of 10¹¹ G Ex. 104 1A 0.5 G Latter half of the order of 10¹⁰ G Ex. 105 3 A 1.49 G Formerhalf of the order of 10¹⁰ G Ex. 106 5 A 2.48 G Former half of the orderof 10¹⁰ G Ex. 107 8 0 0.5 A 0.08 G Latter half of the order of 10¹¹ GEx. 108 1 A 0.16 G Former half of the order of 10¹¹ G Ex. 109 3 A 0.49 GLatter half of the order of 10¹⁰ G Ex. 110 5 A 0.81 G Latter half of theorder of 10¹⁰ GSilicone Adhesive Composition I-β

In Comparative Examples 81(I) to 89(I), ioninc liquid A was used in anamount of 3 parts by mass. In Comparative Examples 90(I) to 92(I), noioninc liquid was used. The results are as shown in Table 23(I). Theterm “(I)” in the Comparative Example numbers is omitted in this Table.

TABLE 23(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample m n mass Type mass mass Curability Surface resistivity strengthComp. Ex. 81 2 0 0.4 A 3 0.2 NG Former half of the order of 10¹² — Comp.Ex. 82 0 0.5 0.25 NG Former half of the order of 10¹² — Comp. Ex. 83 0 10.5 NG Latter half of the order of 10¹¹ — Comp. Ex. 84 0 3 1.49 NGLatter half of the order of 10¹⁰ — Comp. Ex. 85 8 0 0.4 0.03 NG Formerhalf of the order of 10¹⁰ — Comp. Ex. 86 0 0.5 0.08 NG Former half ofthe order of 10¹² — Comp. Ex. 87 0 1 0.16 NG Latter half of the order of10¹¹ — Comp. Ex. 88 0 3 0.49 NG Former half of the order of 10¹¹ — Comp.Ex. 89 0 5 0.81 NG Latter half of the order of 10¹⁰ — Comp. Ex. 90 2 00.5 — 0.25 G Former half of the order of 10¹⁴ G Comp. Ex. 91 0 5 2.48 GFormer half of the order of 10¹⁴ G Comp. Ex. 92 0 6 2.97 G Former halfof the order of 10¹⁴ NGSilicone Adhesive Composition I-β

In Comparative Examples 93(I) to 96(I), no polyoxyalkylene compound wasused. In Comparative Example 97(I), neither polyoxyalkylene compound norioninc liquid was used. The results are as shown in Table 24(I). Theterm “(I)” in the Comparative Example numbers is omitted in this Table.

TABLE 24(I) Component (B1) Component (C) Component (c2) Amount, Amount,Amount, Evaluation results Comparative part by part by part by BondExample m n mass Type mass mass Curability Surface resistivity strengthComp. Ex. 93 — A 0.5 — G Former half of the order of 10¹³ G Comp. Ex. 941 G Former half of the order of 10¹³ G Comp. Ex. 95 3 G Former half ofthe order of 10¹³ G Comp. Ex. 96 5 G Former half of the order of 10¹³ GComp. Ex. 97 — — G 10¹⁵ or more GSilicone Adhesive Composition I-β

In Comparative Examples 98(I) to 108(I), the lithium salt wassubstituted for component (C). The results are as shown in Table 25(I).The term “(I)” in the Comparative Example numbers is omitted in thisTable.

TABLE 25(I) Component (B1) Lithium salt Component (c2) Amount, Amount,Amount a Evaluation results Comparative part by part by part by BondExample m n mass mass mass Curability Surface resistivity strength Comp.Ex. 98 2 0 0.4 0.5 0.1 G Former half of the order of 10¹¹ NG Comp. Ex.99 0.5 0.5 0.25 G Latter half of the order of 10¹⁰ NG Comp. Ex. 100 0.50.05 0.5 G Latter half of the order of 10⁹ NG Comp. Ex. 101 0.5 0.01 0.5G Latter half of the order of 10⁹ NG Comp. Ex. 102 1 0.5 0.5 G Latterhalf of the order of 10⁹ NG Comp. Ex. 103 3 0.5 1.49 G Former half ofthe order of 10⁹ NG Comp. Ex. 104 5 0.5 2.48 G Former half of the orderof 10⁹ NG Comp. Ex. 105 8 0 0.5 0.5 0.08 G Latter half of the order of10¹⁰ NG Comp. Ex. 106 1 0.16 G Former half of the order of 10¹⁰ NG Comp.Ex. 107 5 0.81 G Latter half of the order of 10⁹ NG Comp. Ex. 108 0.40.49 G Former half of the order of 10¹¹ NGSilicone Adhesive Composition I-β

In Comparative Examples 109(I) and 110(I), comparative polyoxyalkylenecompound (1) with m=0 and n=12 was used. In Comparative Examples 111(I)and 112(I), comparative polyoxyalkylene compound (1) with m=22 and n=0was used. The results are as shown in Table 26(I). The term “(I)” in theComparative Example numbers is omitted in this Table.

TABLE 26(I) Polyoxyalkylene compound (1) Component (C) Component (c2)Amount, Amount, Amount, Evaluation results Comparative part by part bypart by Bond Example m n mass Type mass mass Curability Surfaceresistivity strength Comp. Ex. 109 0 12 1 A 0.5 0.16 G Former half ofthe order of 10¹³ NG Comp. Ex. 110 3 0.49 NG Former half of the order of10¹³ — Comp. Ex. 111 22 0 1 0.12 G Former half of the order of 10¹² NGComp. Ex. 112 3 0.37 NG Latter half of the order of 10¹¹ —Silicone Adhesive Composition I-β

In Comparative Examples 113(I) to 118(I), comparative polyoxyalkylenecompound (a) or (b) having one unsaturated hydrocarbon group and onepolyoxyalkylene residue in one molecule was used. The results are asshown in Table 27(I). The term “(I)” in the Comparative Example numbersis omitted in this Table.

TABLE 27(I) Polyoxyalkylene compound Component (C) Component (c2)Amount, Amount, Amount, Evaluation results Comparative part by part bypart by Bond Example Type mass Type mass mass Curability Surfaceresistivity strength Comp. Ex. 113 (a) 0.5 A 0.5 0.14 G Latter half ofthe order of 10¹² NG Comp. Ex. 114 1 A 0.5 0.27 G Former half of theorder of 10⁹ NG Comp. Ex. 115 3 A 0.5 0.82 G Former half of the order of10⁹ NG Comp. Ex. 116 (b) 0.5 A 0.5 0.13 G Latter half of the order of10¹² NG Comp. Ex. 117 1 A 0.5 0.26 G Former half of the order of 10⁹ NGComp. Ex. 118 3 A 0.5 0.78 G Former half of the order of 10⁹ NGSilicone Adhesive Composition I-β

In Comparative Examples 119(I) to 124(I), comparative polyoxyalkylenecompound (c) or (d) having one polyoxyalkylene residue in one moleculewas used. The results are as shown in Table 28(I). The term “(I)” in theComparative Example numbers is omitted in this Table.

TABLE 28(I) Polyoxyalkylene compound Component (C) Component (c2)Amount, Amount, Amount, Evaluation results part by part by part by BondType mass Type mass mass Curability Surface resistivity strength Comp.Ex. 119 (c) 0.5 A 0.5 0.25 G Latter half of the order of 10¹³ G Comp.Ex. 120 1 0.49 G Former half of the order of 10¹³ G Comp. Ex. 121 5 2.47NG Latter half of the order of 10¹² — Comp. Ex. 122 (d) 0.5 0.13 GLatter half of the order of 10¹³ G Comp. Ex. 123 1 0.27 G Former half ofthe order of 10¹³ G Comp. Ex. 124 5 1.34 NG Latter half of the order of10¹² —Silicone Adhesive Composition I-α

In Comparative Examples 125(I) to 132(I), comparative polyoxyalkylenecompound (e) having two polyoxyalkylene residues and no unsaturatedhydrocarbon group in one molecule was used to obtain silicone adhesivecompositions α. The results are as shown in Table 29(I). The term “(I)”in the Comparative Example numbers is omitted in this Table.

TABLE 29(I) Polyoxyalkylene compound Component (C) Component (c2)Amount, Amount, Amount, Evaluation results Comparative part by part bypart by Bond Example Type mass Type mass mass Curability Surfaceresistivity strength Comp. Ex. 125 (e) 0.5 A 0.5 0 NG Latter half of theorder of 10¹¹ — Comp. Ex. 126 1 0 NG Latter half of the order of 10¹⁰ —Comp. Ex. 127 3 0 NG Former half of the order of 10¹⁰ — Comp. Ex. 128 50 NG Former half of the order of 10¹⁰ — Comp. Ex. 129 0.5 A 0.5 0.25 NGLatter half of the order of 10¹¹ — Comp. Ex. 130 1 0.5 NG Latter half ofthe order of 10¹⁰ — Comp. Ex. 131 3 1.49 NG Former half of the order of10¹⁰ — Comp. Ex. 132 5 2.48 NG Former half of the order of 10¹⁰ —Silicone Adhesive Composition I-β

In Comparative Examples 133(I) to 140(I), comparative polyoxyalkylenecompound (e) having two polyoxyalkylene residues and no unsaturatedhydrocarbon group in one molecule was used to obtain silicone adhesivecompositions β. The results are as shown in Table 30(I). The term “(I)”in the Comparative Example numbers is omitted in this Table.

TABLE 30(I) Polyoxyalkylene compound Component (C) Component (c2)Amount, Amount, Amount, Evaluation results Comparative part by part bypart by Bond Example Type mass Type mass mass Curability Surfaceresistivity strength Comp. Ex. 133 (e) 0.5 A 0.5 0 NG Latter half of theorder of 10¹³ — Comp. Ex. 134 1 0 NG Former half of the order of 10¹³ —Comp. Ex. 135 3 0 NG Latter half of the order of 10¹² — Comp. Ex. 136 50 NG Latter half of the order of 10¹³ — Comp. Ex. 137 0.5 A 0.5 0.25 NGLatter half of the order of 10¹³ — Comp. Ex. 138 1 0.5 NG Former half ofthe order of 10¹³ — Comp. Ex. 139 3 1.49 NG Latter half of the order of10¹² — Comp. Ex. 140 5 2.48 NG Latter half of the order of 10¹³ —

As shown in Tables 11(I) and 25(I), the silicone adhesive compositionscomprising the lithium salt had the poor strengths of bond to the sheetsubstrate and, therefore, caused residual adhesives on the sheet-stuckbody. In contrast, the present adhesive compositions comprising theioninc liquid and the oxyalkylene compound had the good strengths ofbond to the sheet substrate and, therefore, caused no residual adhesiveon the sheet-stuck body. As shown in Tables 10(I) and 24(I), the curedproducts of the silicone adhesive compositions comprising neither ionincliquid nor oxyalkylene compound had the high surface resistivities of10¹⁵, i.e., 1E+15 Ω/sq., or more, and the cured products of the siliconeadhesive compositions comprising the ionic liquid with no oxyalkylenecompound had the less decreased surface resistivities of a former halfof the order of 10¹³, i.e., 1E+13 to 5E+13 Ω/sq. In contrast, the cured,products of the present compositions comprising a combination of theoxyalkylene compound with the ionic liquid had the low surfaceresistivities of a former half of the order of 10¹⁰ to a latter half ofthe order of 10¹², i.e., 1E+10 to 9.9E+12 Ω/sq., and the excellentantistatic properties, as shown in the Examples.

As shown in Tables 29(I) and 30(I), the adhesive compositions comprisingthe oxylalkylene compound having no unsaturated hydrocarbon group wereinferior in the curability. This is because the oxyalkylene compound haspoor compatibility with the compositions. As shown in Tables 13(I) and27(I), the cured products of the compositions comprising the oxyalkylenecompound having one polyoxyalkylene residue and one unsaturatedhydrocarbon group had the poor strengths of bond to the sheet substrate,though they had the low surface resistivities. As shown in Tables 14(I)and 28(I), the cured products of the adhesive compositions comprisingthe oxyalkylene compound having one polyoxyalkylene residue and twounsaturated hydrocarbon groups had the high surface resistivities,though they had the good strengths of bond to the sheet substrate. Incontrast, the present adhesive compositions comprising the oxyalkylenecompound had the good strengths of bond to the sheet substrate and thelow surface resistivities. Thus, it is important for the oxyalkylenecompound to have two polyoxyalkylene residues and two unsaturatedhydrocarbon groups, in order to provide an adhesive layer which isexcellent in an antistatic property and a strength of bond to a sheetsubstrate.

Part II: Second Embodiment

The Examples and the Comparative Examples for the second embodiment aredescribed in Part II. Components used in the Examples and theComparative Examples are as follows. The viscosity was hereinafterdetermined at 25 degrees C. with a Brookfield rotary viscometer of theBM type.

(A) Addition Reaction-Curable Silicone

-   -   Polysiloxane (a1): vinyl group-containing polydimethylsiloxane        with the molecular chain terminals each capped with a        dimethylvinylsilyl (SiMe₂Vi) group, having a viscosity of 27000        mPa·s in a 30% solution in toluene and a vinyl group content of        0.075 mole %    -   Polysiloxane (a2): vinyl group-containing polydimethylsiloxane        with the molecular chain terminals each capped with a        dimethylvinylsilyl (SiMe₂Vi) group, having a viscosity of 27000        mPa·s in a 30% solution in toluene and a vinyl group content of        0.15 mole %    -   Polysiloxane (b): a 60% solution of polysilosane composed of        Me₃SiO_(0.5) units and SiO₂ units (Me₃SiO_(0.5) units/SiO₂        units=0.82), in toluene    -   Polysiloxane (c1): organohydrogenpolysiloxane represented by the        following formula:

-   -   Polysiloxane (c2): organohydrogenpolysiloxane represented by the        following formula:

Component (B): polyoxyalkylene represented by the following formulas:(B-1): polyoxyalkylene having one unsaturated hydrocarbon group andrepresented by the following formula (a) or (b):CH₂═CH—CH₂—O—(C₂H₄O)_(m)—(C₃H₆O)_(n)—H  (a)wherein m and n are a combination of (m,n)=(8,0), (16,0), (0,10) or(12,2). The combination of m and n in the polyoxyalkylene used in theExamples and the Comparative Examples is as shown in the followingTables.CH₂═CH—CH₂—O—(C₂H₄O)_(m)—(C₃H₆O)_(n)—CH₃  (b)wherein m and n is (m,n)=(6,0).(B-2): polyoxyalkylene having two unsaturated hydrocarbon groups andrepresented by the following formula (c):CH₂═CH—CH₂—O—(C₂H₄O)_(m)—(C₃H₆O)_(n)—CH₂—CH═CH₂  (c)wherein m and n are a combination of (m,n)=(8,0), (16,0), (0,10) or(12,2). The combination of m and n in the polyoxyalkylene used in theExamples and the Comparative Examples is as shown in the followingTables.(B-3): polyoxyalkylene represented by the following formula:

wherein m and n are a combination of (m/n)=(2,0), (10,0) or (20,0). Thecombination of m and n in component (B) used in the Examples and theComparative Examples is as shown in the following Tables.Component (C):

-   -   Ionic liquid A: trimethylpropylammonium        bis(trifluoromethanesulfonyl)imide    -   Ionic liquid B: butyltrimethylammonium bis(trifluoromethyl        sulfonyl)imide    -   Ionic liquid C: ethyldimethylpropylammonium        bis(trifluoromethylsulfonyl)imide        Catalyst:    -   Platinum catalyst A: a solution of chloroplatinic acid in        1-butanol    -   Platinum catalyst B: a solution of chloroplatinic acid in        2-ethylhexyl alcohol    -   Comparative catalyst C: a reaction product (complex) of        chloroplatinic acid with a vinyl group-containing siloxane

Preparation Example II-1

Preparation of Silicone Adhesive Composition (II-α)

Forty parts by mass of polysiloxane (a1), 83.3 parts by mass ofpolysiloxane (b), 0.4 part by mass of polysiloxane (c1) and 33.3 partsby mass of toluene were mixed to obtain a solution, to which 0.2 part bymass of 1-ethynylcyclohexanol was added and mixed to obtain a mixturehaving a siloxane content of approximately 60% by mass at a ratio of thenumber of the SiH groups in component (c1) to the number of the alkenylgroups in component (a2) of 15. To 100 parts by mass of the mixture, the(poly)oxyalkylene shown in the following Tables, ionic liquid (C) shownin the Tables, and polysiloxane (c2) were added in the amounts in partby mass shown in the Tables, and then stirred to obtain a homogeneousmixture. To 100 parts by mass of the mixture, 50 parts by mass oftoluene were added, and then mixed to prepare a mixture having asiloxane content of approximately 40% by mass. The catalyst shown in theTables was added so that the mass of platinum atoms was 250 ppm relativeto a total mass of components (a) and (b), and then stirred enough toobtain a silicone adhesive composition (II-α). It is noted that theamount of polysiloxane (c2) was such that a ratio of the number of theSiH groups in polysiloxane (c2) to the number of the alkenyl groups incomponent (B) was 1.

Preparation Example II-2

Preparation of Silicone Adhesive Composition (II-β)

Ninety five parts by mass of polysiloxane (a2), 8.3 parts by mass ofpolysiloxane (b), 0.6 part by mass of polysiloxane (c1) and 33.3 partsby mass of toluene were mixed to obtain a solution, to which 0.2 part bymass of 1-ethynylcyclohexanol was added to obtain a mixture having asiloxane content of approximately 60% by mass at a ratio of the numberof the SiH groups in component (c1) to the number of the alkenyl groupsin component (a2) of 5. To 100 parts by mass of the mixture, the(poly)oxylalkylene shown in the following Tables, ionic liquid (C) shownin the Tables, and polysiloxane (c2) were added in the amounts in partby mass shown in the Tables, and then stirred to obtain a homogeneousmixture. To 100 parts by mass of the mixture, 50 parts by mass oftoluene were added, and then mixed to prepare a mixture having asiloxane content of approximately 40% by mass. The catalyst shown in theTables was added so that the mass of platinum atoms was 250 ppm relativeto a total mass of components (a) and (b), and then stirred enough toobtain a silicone adhesive composition (II-β). It is noted that theamount of polysiloxane (c2) was such that a ratio of the number of theSiH groups in polysiloxane (c2) to the number of the alkenyl groups incomponent (B) was 1.

The silicone adhesive compositions obtained above were subjected to thefollowing tests.

Curability

The silicone adhesive composition was applied on a polyimide film havinga dimension of 110 mm×110 mm and a thickness of 25 μm with an applicatorso as to provide a coating having a thickness of 30 μm and, then, heatedat 130 degrees C. to prepare an adhesive sheet. The heating time was 1minute, 3 minutes or 5 minutes. Each of the adhesive sheet was put on asurface of stainless steel of SUS304 polished with grade #280 sandpaperand, then, pressed by one cycle of going and returning of a 2 kg roller.Then, the adhesive sheet was peeled from the stainless steel surface toevaluate curability. In a case where no adhesive remained on thestainless steel surface, curing proceeded sufficiently and no adhesivetransferred to the substrate. Curability was evaluated as G. Meanwhilein a case where some adhesive remained on the stainless steel surface,curing did not sufficiently proceed and some adhesive transferred to thesubstrate. Curability was evaluated as NG. Also in a case where curingwas not completed even after heating for 5 minutes, curability wasevaluated as NG.

Surface Resistivity

The silicone adhesive composition was applied on a polyimide film havinga dimension of 110 mm×110 mm and a thickness of 25 μm with an applicatorso as to provide a coating having a thickness of 30 μm and, then, heatedat 130 degrees C. for 2 minutes to be cured, to thereby prepare anadhesive sheet. The surface resistivity of the adhesive sheet wasdetermined in the same manner as in Part I. The results are shown in thefollowing Tables in the same manner as in Part I.

The evaluation results of the various silicone adhesive compositions(II-α) are as shown in the following Tables 1(II) to 15(II) and 30(II)to 32(II). The evaluation results of the various silicone adhesivecompositions (II-β) are as shown in the following Tables 16(II) to29(II).

Silicone Adhesive Composition II-α

The following Tables 1(II) to 10(II) show the cases wherepolyoxyalkylene (B-1) having one unsaturated hydrocarbon group was used.In Examples 1(II) to 4(II) and Comparative Examples 1(II) and 2(II),polyoxyalkylene (a) with m=8 and n=0, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. In Examples5(II) to 8(II) and Comparative Examples 3(II) and 4(II), polyoxyalkylene(a) with m=16 and n=0, ioninc liquid A and catalyst A were used in thevarious amounts of the polyoxyalkylene. The results are as shown inTable 1(II). The term “(II)” in the Example and Comparative Examplenumbers is omitted in this Table.

TABLE 1(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 8 0 0.4 A 0.5 0.06 G G G Formerhalf of the order of 10¹³ Ex. 1 Ex. 1 0.5 0.08 G G G Latter half of theorder of 10¹² Ex. 2 1 0.16 G G G Former half of the order of 10⁹ Ex. 3 30.47 G G G Former half of the order of 10⁹ Ex. 4 5 0.78 G G G Formerhalf of the order of 10⁹ Comp. 6 0.94 NG NG G Former half of the orderof 10⁹ Ex. 2 Comp. 16 0 0.4 0.03 G G G Former half of the order of 10¹³Ex. 3 Ex. 5 0.5 0.04 G G G Latter half of the order of 10¹⁰ Ex. 6 1 0.08G G G Latter half of the order of 10⁹ Ex. 7 3 0.25 G G G Latter half ofthe order of 10⁹ Ex. 8 5 0.42 G G G Latter half of the order of 10⁹Comp. 6 0.5 NG NG G Latter half of the order of 10⁹ Ex. 4Silicone Adhesive Composition II-α

In Examples 9(II) to 12(II) and Comparative Examples 5(II) and 6(II),polyoxyalkylene (a) with m=0 and n=10, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. In Examples13(II) to 16(II) and Comparative Examples 7(II) and 8(II),polyoxyalkylene (a) with m=12 and n=2, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. The results areas shown in Table 2(II). The term “(II)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 2(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 0 10 0.4 A 0.5 0.04 G G G Formerhalf of the order of 10¹³ Ex. 5 Ex. 9 0.5 0.05 G G G Latter half of theorder of 10⁹ Ex. 10 1 0.1 G G G Latter half of the order of 10⁹ Ex. 11 30.3 G G G Latter half of the order of 10⁹ Ex. 12 5 0.5 G G G Latter halfof the order of 10⁹ Comp. 6 0.6 NG NG G Latter half of the order of 10⁹Ex. 6 Comp. 12 2 0.4 0.04 G G G Former half of the order of 10¹³ Ex. 7Ex. 13 0.5 0.05 G G G Former half of the order of 10¹⁰ Ex. 14 1 0.09 G GG Former half of the order of 10¹⁰ Ex. 15 3 0.27 G G G Former half ofthe order of 10¹⁰ Ex. 16 5 0.46 G G G Former half of the order of 10¹⁰Comp. 6 0.55 NG NG G Former half of the order of 10¹⁰ Ex. 8Silicone Adhesive Composition II-α

In Examples 17(II) to 20(II) and Comparative Examples 9(II) and 10(II),polyoxyalkylene (b) with m=6 and n=0, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. The results areas shown in Table 3(II). The term “(II)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 3(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Surface Example Example Catalyst m n mass Typemass mass 1 3 5 resistivity Comp. Ex. 9 A 6 0 0.4 A 0.5 0.08 G G GFormer half of the order of 10¹³ Ex. 17 0.5 0.1 G G G Former half of theorder of 10¹⁰ Ex. 18 1 0.19 G G G Former half of the order of 10¹⁰ Ex.19 3 0.58 G G G Former half of the order of 10¹⁰ Ex. 20 5 0.96 G G GFormer half of the order of 10¹⁰ Comp. Ex. 10 6 1.15 NG NG G Former halfof the order of 10¹⁰Silicone Adhesive Composition II-α

In Comparative Examples 11(II) to 25(II), ioninc liquid A andcomparative catalyst C were used together with component (B-1) shown inthe following Table in the various amounts. As component (B-1), compound(a) was used in Comparative Examples 11(II) to 21(II), and compound (b)was used in Comparative Examples 22(II) to 25(II). The results are asshown in Table 4(II). The term “(II)” in the Comparative Example numbersis omitted in this Table.

TABLE 4(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Catalyst m n mass Type mass mass 1 3 5Surface resistivity Comp. Ex. 11 C 8 0 0.5 A 0.5 0.08 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 12 8 0 1 0.16 NG NG G Former half ofthe order of 10⁹ Comp. Ex. 13 8 0 3 0.47 NG NG NG Former half of theorder of 10⁹ Comp. Ex. 14 16 0 0.5 0.04 NG NG G Latter half of the orderof 10¹⁰ Comp. Ex. 15 16 0 1 0.08 NG NG G Latter half of the order of 10⁹Comp. Ex. 16 16 0 3 0.25 NG NG NG Latter half of the order of 10⁹ Comp.Ex. 17 0 10 0.5 0.05 NG NG G Latter half of the order of 10⁹ Comp. Ex.18 0 10 1 0.1 NG NG G Latter half of the order of 10⁹ Comp. Ex. 19 12 20.5 0.05 NG NG G Former half of the order of 10¹⁰ Comp. Ex. 20 12 2 10.09 NG NG G Former half of the order of 10¹⁰ Comp. Ex. 21 12 2 3 0.27NG NG NG Former half of the order of 10¹⁰ Comp. Ex. 22 6 0 0.5 0.1 NG NGG Former half of the order of 10¹⁰ Comp. Ex. 23 6 0 1 0.19 NG NG GFormer half of the order of 10¹⁰ Comp. Ex. 24 6 0 3 0.58 NG NG NG Formerhalf of the order of 10¹⁰ Comp. Ex. 25 6 0 5 0.96 NG NG NG Former halfof the order of 10¹⁰Silicone Adhesive Composition II-α

In Examples 21(II) to 32(II) and Comparative Examples 26(II) and 27(II),ioninc liquid B or C in an amount of 0.5 part by mass and catalyst Awere used together with component (B-1) shown in the following Table inthe various amounts. The results are as shown in Table 5(II). The term“(II)” in the Example and Comparative Example numbers is omitted in thisTable.

TABLE 5(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Comp. Ex. 26 A 8 0 0.4 B 0.5 0.06 G G GFormer half of the order of 10¹³ Ex. 21 8 0 0.5 0.08 G G G Latter halfof the order of 10¹² Ex. 22 8 0 1 0.16 G G G Former half of the order of10⁹ Ex. 23 8 0 3 0.47 G G G Former half of the order of 10⁹ Ex. 24 8 0 50.78 NG G G Former half of the order of 10⁹ Comp. Ex. 27 8 0 6 0.94 NGNG NG Former half of the order of 10⁹ Ex. 25 16 0 0.5 0.04 G G G Latterhalf of the order of 10⁹ Ex. 26 16 0 5 0.42 NG G G Latter half of theorder of 10⁹ Ex. 27 8 0 0.5 C 0.08 G G G Latter half of the order of10¹² Ex. 28 8 0 1 0.16 G G G Former half of the order of 10⁹ Ex. 29 8 03 0.47 G G G Former half of the order of 10⁹ Ex. 30 8 0 5 0.78 NG G GFormer half of the order of 10⁹ Ex. 31 16 0 0.5 0.04 G G G Latter halfof the order of 10⁹ Ex. 32 16 0 5 0.42 NG G G Latter half of the orderof 10⁹Silicone Adhesive Composition II-α

In Comparative Examples 28(II) to 39(II), catalyst C was substituted forcatalyst A in Examples 21(II) to 32(II). The results are as shown inTable 6(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 6(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Catalyst m n mass Type mass mass 1 3 5Surface resistivity Comp. Ex. 28 C 8 0 0.5 B 0.5 0.08 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 29 8 0 1 0.16 NG NG G Former half ofthe order of 10⁹ Comp. Ex. 30 8 0 3 0.47 NG NG NG Former half of theorder of 10⁹ Comp. Ex. 31 8 0 5 0.78 NG NG NG Former half of the orderof 10⁹ Comp. Ex. 32 16 0 0.5 0.04 NG NG G Latter half of the order of10⁹ Comp. Ex. 33 16 0 5 0.42 NG NG NG Latter half of the order of 10⁹Comp. Ex. 34 8 0 0.5 C 0.08 NG NG G Latter half of the order of 10¹²Comp. Ex. 35 8 0 1 0.16 NG NG G Former half of the order of 10⁹ Comp.Ex. 36 8 0 3 0.47 NG NG NG Former half of the order of 10⁹ Comp. Ex. 3716 0 0.5 0.04 NG NG G Latter half of the order of 10⁹ Comp. Ex. 38 16 01 0.08 NG NG G Latter half of the order of 10⁹ Comp. Ex. 39 16 0 3 0.25NG NG NG Latter half of the order of 10⁹Silicone Adhesive Composition II-α

In Examples 33(II) to 40(II), ioninc liquid A was used in an amount of0.01 part by mass or 2 parts by mass. The results are as shown in Table7(II). The term “(II)” in the Example numbers is omitted in this Table.

TABLE 7(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, part by part bypart by minute Example Catalyst m n mass Type mass mass 1 3 5 Surfaceresistivity Ex. 33 A 8 0 0.5 A 0.01 0.08 G G G Latter half of the orderof 10¹² Ex. 34 8 0 5 0.78 G G G Former half of the order of 10¹² Ex. 3516 0 0.5 0.04 G G G Latter half of the order of 10¹² Ex. 36 16 0 5 0.42G G G Latter half of the order of 10¹² Ex. 37 8 0 0.5 2 0.08 G G GLatter half of the order of 10¹² Ex. 38 8 0 5 0.78 G G G Former half ofthe order of 10⁹ Ex. 39 16 0 0.5 0.04 G G G Latter half of the order of10⁹ Ex. 40 16 0 5 0.42 G G G Latter half of the order of 10⁹Silicone Adhesive Composition II-α

In Comparative Examples 40(II) to 45(II), ioninc liquid A was used inthe amount of more than the upper limit. In Comparative Examples 46(II)to 49(II), no ionic liquid was used. The results are as shown in Table8(II). The term “(II)” in the Comparative Example numbers is omitted inthis Table.

TABLE 8(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Catalyst m n mass Type mass mass 1 3 5Surface resistivity Comp. Ex. 40 A 8 0 0.5 A 3 0.08 NG G G Latter halfof the order of 10¹² Comp. Ex. 41 8 0 1 0.16 NG G G Former half of theorder of 10⁹ Comp. Ex. 42 8 0 5 0.78 NG G G Former half of the order of10⁹ Comp. Ex. 43 16 0 0.5 0.04 NG G G Latter half of the order of 10⁹Comp. Ex. 44 16 0 3 0.25 NG G G Latter half of the order of 10⁹ Comp.Ex. 45 16 0 5 0.42 NG G G Latter half of the order of 10⁹ Comp. Ex. 46 80 0.5 0 0.08 G G G Former half of the order of 10¹⁴ Comp. Ex. 47 8 0 10.16 G G G Former half of the order of 10¹⁴ Comp. Ex. 48 8 0 3 0.47 G GG Former half of the order of 10¹⁴ Comp. Ex. 49 8 0 5 0.78 G G G Formerhalf of the order of 10¹⁴Silicone Adhesive Composition II-α

In Comparative Examples 50(II) to 57(II), comparative catalyst C wassubstituted for catalyst A in Examples 33(II) to 40(II). The results areas shown in Table 9(II). The term “(II)” in the Comparative Examplenumbers is omitted in this Table.

TABLE 9(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Catalyst m n mass Type mass mass 1 3 5Surface resistivity Comp. Ex. 50 C 8 0 0.5 A 0.01 0.08 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 51 8 0 5 0.78 NG NG G Former half ofthe order of 10¹² Comp. Ex. 52 16 0 0.5 0.04 NG NG G Latter half of theorder of 10¹² Comp. Ex. 53 16 0 5 0.42 NG NG G Latter half of the orderof 10¹² Comp. Ex. 54 8 0 0.5 2 0.08 NG NG G Latter half of the order of10¹² Comp. Ex. 55 8 0 5 0.78 NG NG G Former half of the order of 10⁹Comp. Ex. 56 16 0 0.5 0.04 NG NG G Latter half of the order of 10⁹ Comp.Ex. 57 16 0 5 0.42 NG NG G Latter half of the order of 10⁹Silicone Adhesive Composition II-α

In Examples 41(II) to 53(II) and Comparative Examples 58(II) to 60(II),catalyst B was used. The results are as shown in Table 10(II). The term“(II)” in the Example and Comparative Example numbers is omitted in thisTable.

TABLE 10(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Ex. 41 B 8 0 5 A 0.5 0.78 G G G Formerhalf of the order of 10⁹ Ex. 42 0 10 5 A 0.5 G G G Latter half of theorder of 10⁹ Ex. 43 12 2 0.5 A 0.05 G G G Former half of the order of10¹⁰ Ex. 44 6 0 0.5 A 0.1 G G G Former half of the order of 10¹⁰ Ex. 458 0 0.5 B 0.08 G G G Latter half of the order of 10¹² Ex. 46 16 0 5 B0.42 NG G G Latter half of the order of 10⁹ Ex. 47 8 0 5 C 0.78 NG G GFormer half of the order of 10⁹ Ex. 48 16 0 5 C 0.42 NG G G Latter halfof the order of 10⁹ Ex. 49 8 0 0.5 A 0.01 0.08 G G G Latter half of theorder of 10¹² Ex. 50 16 0 0.5 A 0.04 G G G Latter half of the order of10¹² Ex. 51 8 0 5 A 2 0.78 G G G Former half of the order of 10⁹ Ex. 5216 0 0.5 A 0.04 G G G Latter half of the order of 10⁹ Ex. 53 16 0 5 A0.42 G G G Latter half of the order of 10⁹ Comp. Ex. 58 8 0 0.5 A 3 0.08NG NG G Latter half of the order of 10¹² Comp. Ex. 59 16 0 5 A 0.42 NGNG G Latter half of the order of 10⁹ Comp. Ex. 60 8 0 5 A 0 0.78 G G GFormer half of the order of 10¹⁴Silicone Adhesive Composition II-α

The following Tables 11(II) to 15(II) show the cases wherepolyoxyalkylene (B-2) having two unsaturated hydrocarbon groups wasused. In Examples 54(II) to 57(II) and Comparative Examples 61(II) and62(II), polyoxyalkylene (a) with m=8 and n=0, ioninc liquid A andcatalyst A were used in the various amounts of the polyoxyalkylene. InExamples 58(II) to 61(II) and Comparative Examples 63(II) and 64(II),polyoxyalkylene (a) with m=16 and n=0, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. The results areas shown in Table 11(II). The term “(II)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 11(II) Component Evaluation results Component (B-2) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Comp. Ex. 61 A 8 0 0.4 A 0.5 0.06 G G GFormer half of the order of 10¹³ Ex. 54 0.5 0.07 G G G Latter half ofthe order of 10¹² Ex. 55 1 0.15 G G G Former half of the order of 10⁹Ex. 56 3 0.44 G G G Former half of the order of 10⁹ Ex. 57 5 0.74 G G GFormer half of the order of 10⁹ Comp. Ex. 62 6 0.88 NG NG G Former halfof the order of 10⁹ Comp. Ex. 63 16 0 0.4 0.03 G G G Former half of theorder of 10¹³ Ex. 58 0.5 0.04 G G G Latter half of the order of 10¹⁰ Ex.59 1 0.08 G G G Latter half of the order of 10⁹ Ex. 60 3 0.24 G G GLatter half of the order of 10⁹ Ex. 61 5 0.41 G G G Latter half of theorder of 10⁹ Comp. Ex. 64 6 0.49 NG NG G Latter half of the order of 10⁹Silicone Adhesive Composition II-α

In Examples 62(II) to 65(II) and Comparative Examples 65(II) and 66(II),polyoxyalkylene (a) with m=0 and n=10, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. In Examples66(II) to 69(II) and Comparative Examples 67(II) and 68(II),polyoxyalkylene (a) with m=12 and n=0, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. The results areas shown in Table 12(II). The term “(II)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 12(II) Component Evaluation results Component (B-2) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Comp. Ex. 65 A 0 10 0.4 A 0.5 0.04 G G GFormer half of the order of 10¹³ Ex. 62 0.5 0.05 G G G Latter half ofthe order of 10⁹ Ex. 63 1 0.1 G G G Latter half of the order of 10⁹ Ex.64 3 0.29 G G G Latter half of the order of 10⁹ Ex. 65 5 0.48 G G GLatter half of the order of 10⁹ Comp. Ex. 66 6 0.58 NG NG G Latter halfof the order of 10⁹ Comp. Ex. 67 12 2 0.4 0.04 G G G Former half of theorder of 10¹³ Ex. 66 0.5 0.04 G G G Former half of the order of 10¹⁰ Ex.67 1 0.09 G G G Former half of the order of 10¹⁰ Ex. 68 3 0.26 G G GFormer half of the order of 10¹⁰ Ex. 69 5 0.44 G G G Former half of theorder of 10¹⁰ Comp. Ex. 68 6 0.53 NG NG G Former half of the order of10¹⁰Silicone Adhesive Composition II-α

In Comparative Examples 69(II) to 82(II), ioninc liquid A andcomparative catalyst C were used together with component (B-2) shown inthe following Table in the various amounts. The results are as shown inTable 13(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 13(II) Component Evaluation results Component (B-2) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Catalyst m n mass Type mass mass 1 3 5Surface resistivity Comp. Ex. 69 C 8 0 0.5 A 0.5 0.07 NG NG G Latterhalf of the order of 10¹³ Comp. Ex. 70 8 0 1 A 0.5 0.15 NG NG G Formerhalf of the order of 10¹³ Comp. Ex. 71 8 0 3 A 0.5 0.44 NG NG NG Latterhalf of the order of 10¹² Comp. Ex. 72 8 0 5 A 0.5 0.74 NG NG NG Latterhalf of the order of 10¹² Comp. Ex. 73 8 0 6 A 0.5 0.88 NG NG NG Formerhalf of the order of 10¹² Comp. Ex. 74 16 0 0.4 A 0.5 0.03 NG NG GLatter half of the order of 10¹³ Comp. Ex. 75 16 0 0.5 A 0.5 0.04 NG NGG Former half of the order of 10¹³ Comp. Ex. 76 16 0 1 A 0.5 0.08 NG NGG Latter half of the order of 10¹² Comp. Ex. 77 16 0 3 A 0.5 0.24 NG NGNG Latter half of the order of 10¹² Comp. Ex. 78 0 10 5 A 0.5 0.41 NG NGNG Latter half of the order of 10¹² Comp. Ex. 79 12 2 0.5 A 0.5 0.05 NGNG G Latter half of the order of 10¹² Comp. Ex. 80 12 2 1 A 0.5 0.1 NGNG G Latter half of the order of 10¹² Comp. Ex. 81 12 2 3 A 0.5 0.29 NGNG NG Latter half of the order of 10¹² Comp. Ex. 82 12 2 5 A 0.5 0.48 NGNG NG Latter half of the order of 10¹²Silicone Adhesive Composition II-α

In Examples 70(II) to 81(II) and Comparative Examples 83(II) and 84(II),ioninc liquid B or C was used. The results are as shown in Table 14(II).The term “(II)” in the Example and Comparative Example numbers isomitted in this Table.

TABLE 14(II) Component Evaluation results Component (B-2) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Comp. Ex. 83 A 8 0 0.4 B 0.5 0.06 G G GFormer half of the order of 10¹³ Ex. 70 8 0 0.5 0.07 G G G Latter halfof the order of 10¹² Ex. 71 8 0 1 0.15 G G G Former half of the order of10¹² Ex. 72 8 0 3 0.44 G G G Former half of the order of 10¹² Ex. 73 8 05 0.74 NG G G Former half of the order of 10¹² Comp. Ex. 84 8 0 6 0.88NG NG NG Former half of the order of 10¹² Ex. 74 16 0 0.5 0.04 G G GLatter half of the order of 10¹² Ex. 75 16 0 5 0.41 NG G G Latter halfof the order of 10¹² Ex. 76 8 0 0.5 C 0.07 G G G Latter half of theorder of 10¹² Ex. 77 8 0 1 0.15 G G G Former half of the order of 10¹²Ex. 78 8 0 3 0.44 G G G Former half of the order of 10¹² Ex. 79 8 0 50.74 NG G G Former half of the order of 10¹² Ex. 80 16 0 0.5 0.04 G G GLatter half of the order of 10¹² Ex. 81 16 0 5 0.41 NG G G Latter halfof the order of 10¹²Silicone Adhesive Composition II-α

In Comparative Examples 85(II) to 93(II), catalyst C was substituted forcatalyst A in Examples 70(II) to 81(II). The results are as shown inTable 15(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 15(II) Component Evaluation results Component (B-2) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Catalyst m n mass Type mass mass 1 3 5Surface resistivity Comp. Ex. 85 C 8 0 0.5 B 0.5 0.07 NG NG G Latterhalf of the order of 10¹³ Comp. Ex. 86 8 0 1 0.15 NG NG G Former half ofthe order of 10¹³ Comp. Ex. 87 8 0 3 0.44 NG NG NG Latter half of theorder of 10¹² Comp. Ex. 88 8 0 5 0.74 NG NG NG Latter half of the orderof 10¹² Comp. Ex. 89 16 0 0.5 0.04 NG NG G Former half of the order of10¹² Comp. Ex. 90 16 0 5 0.41 NG NG NG Latter half of the order of 10¹³Comp. Ex. 91 8 0 0.5 C 0.07 NG NG G Former half of the order of 10¹³Comp. Ex. 92 8 0 1 0.15 NG NG G Latter half of the order of 10¹² Comp.Ex. 93 8 0 3 0.44 NG NG NG Latter half of the order of 10¹²Silicone Adhesive Composition II-β

The following Tables 16(II) to 24(II) show the cases wherepolyoxyalkylene (B-1) having one unsaturated hydrocarbon group was used.In Examples 82(II) to 85(II) and Comparative Examples 94(II) and 95(II),polyoxyalkylene (a) with m=8 and n=0, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. In Examples86(II) to 89(II) and Comparative Examples 96(II) and 97(II),polyoxyalkylene (a) with m=16 and n=0, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. The results areas shown in Table 16(II). The term “(II)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 16(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Comp. Ex. 94 A 8 0 0.4 A 0.5 0.06 G G GFormer half of the order of 10¹³ Ex. 82 0.5 0.08 G G G Latter half ofthe order of 10¹² Ex. 83 1 0.16 G G G Former half of the order of 10⁹Ex. 84 3 0.47 G G G Former half of the order of 10⁹ Ex. 85 5 0.78 G G GFormer half of the order of 10⁹ Comp. Ex. 95 6 0.94 NG NG G Former halfof the order of 10⁹ Comp. Ex. 96 16 0 0.4 0.03 G G G Former half of theorder of 10¹³ Ex. 86 0.5 0.04 G G G Latter half of the order of 10¹⁰ Ex.87 1 0.08 G G G Latter half of the order of 10⁹ Ex. 88 3 0.25 G G GLatter half of the order of 10⁹ Ex. 89 5 0.42 G G G Latter half of theorder of 10⁹ Comp. Ex. 97 6 0.5 NG NG G Latter half of the order of 10⁹Silicone Adhesive Composition II-β

In Examples 90(II) to 93(II) and Comparative Examples 98(II) and 99(II),polyoxyalkylene (a) with m=0 and n=10, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. In Examples94(II) to 97(II) and Comparative Examples 100(II) and 101(II),polyoxyalkylene (a) with m=12 and n=2, ioninc liquid A and catalyst Awere used in the various amounts of the polyoxyalkylene. The results areas shown in Table 17(II). The term “(II)” in the Example and ComparativeExample numbers is omitted in this Table.

TABLE 17(II) Component Evaluation results Component (B-1) Component (C)(c2) Curability, Amount, Amount, Amount, Heating time, Comparative partby part by part by minute Example Example Catalyst m n mass Type massmass 1 3 5 Surface resistivity Comp. Ex. 98 A 0 10 0.4 A 0.5 0.04 G G GFormer half of the order of 10¹³ Ex. 90 0.5 0.05 G G G Latter half ofthe order of 10⁹ Ex. 91 1 0.1 G G G Latter half of the order of 10⁹ Ex.92 3 0.3 G G G Latter half of the order of 10⁹ Ex. 93 5 0.5 G G G Latterhalf of the order of 10⁹ Comp. Ex. 99 6 0.6 NG NG G Latter half of theorder of 10⁹ Comp. Ex. 100 12 9 0.4 0.04 G G G Former half of the orderof 10¹³ Ex. 94 0.5 0.05 G G G Former half of the order of 10¹⁰ Ex. 95 10.09 G G G Former half of the order of 10¹⁰ Ex. 96 3 0.27 G G G Formerhalf of the order of 10¹⁰ Ex. 97 5 0.46 G G G Former half of the orderof 10¹⁰ Comp. Ex. 101 6 0.55 NG NG G Former half of che order of 10¹⁰Silicone Adhesive Composition II-β

In Examples 98(II) to 101(II) and Comparative Examples 102(II) and103(II), polyoxyalkylene (b) with m=6 and n=0, ioninc liquid A andcatalyst A were used in the various amounts of the polyoxyalkylene. Theresults are as shown in Table 18(II). The term “(II)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 18(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 6 0 0.4 A 0.5 0.08 G G G Formerhalf of the order of 10¹³ Ex. 102 Ex. 98 0.5 0.1 G G G Former half ofthe order of 10¹⁰ Ex. 99 1 0.19 G G G Former half of the order of 10¹⁰Ex. 100 3 0.58 G G G Former half of the order of 10¹⁰ Ex. 101 5 0.96 G GG Former half of the order of 10¹⁰ Comp. 6 1.15 NG NG G Former half ofthe order of 10¹⁰ Ex. 103Silicone Adhesive Composition II-β

In Comparative Examples 104(II) to 118(II), ioninc liquid A andcomparative catalyst C were used together with component (B-1) shown inthe following Table in the various amounts. As component (B-1), compound(a) was used in Comparative Examples 104(II) to 114(II), and compound(b) was used in Comparative Examples 115(II) to 118(II). The results areas shown in Table 19(II). The term “(II)” in the Comparative Examplenumbers is omitted in this Table.

TABLE 19(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 104 C 8 0 0.5 A 0.5 0.08 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 105 8 0 1 0.16 NG NG G Former halfof the order of 10⁹ Comp. Ex. 106 8 0 3 0.47 NG NG NG Former half of theorder of 10⁹ Comp. Ex. 107 16 0 0.5 0.04 NG NG G Latter half of theorder of 10¹⁰ Comp. Ex. 108 16 0 1 0.08 NG NG G Latter half of the orderof 10⁹ Comp. Ex. 109 16 0 3 0.25 NG NG NG Latter half of the order of10⁹ Comp. Ex. 110 0 10 0.5 0.05 NG NG G Latter half of the order of 10⁹Comp. Ex. 111 0 10 1 0.1 NG NG G Latter half of the order of 10⁹ Comp.Ex. 112 12 2 0.5 0.05 NG NG G Former half of the order of 10¹⁰ Comp. Ex.113 12 2 1 0.09 NG NG G Former half of the order of 10¹⁰ Comp. Ex. 11412 2 3 0.27 NG NG NG Former half of the order of 10¹⁰ Comp. Ex. 115 6 00.5 0.1 NG NG G Former half of the order of 10¹⁰ Comp. Ex. 116 6 0 10.19 NG NG G Former half of the order of 10¹⁰ Comp. Ex. 117 6 0 3 0.58NG NG NG Former half of the order of 10¹⁰ Comp. Ex. 118 6 0 5 0.96 NG NGNG Former half of the order of 10¹⁰Silicone Adhesive Composition II-β

In Examples 102(II) to 113(II) and Comparative Examples 119(II) and120(II), ioninc liquid B or C in an amount of 0.5 part by mass andcatalyst A were used together with component (B-1) shown in thefollowing Table in the various amounts. The results are as shown inTable 20(II). The term “(II)” in the Example and Comparative Examplenumbers is omitted in this Table.

TABLE 20(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 8 0 0.4 B 0.5 0.06 G G G Formerhalf of the order of 10¹³ Ex. 119 Ex. 102 8 0 0.5 0.08 G G G Latter halfof the order of 10¹² Ex. 103 8 0 1 0.16 G G G Former half of the orderof 10⁹ Ex. 104 8 0 3 0.47 G G G Former half of the order of 10⁹ Ex. 1058 0 5 0.78 NG G G Former half of the order of 10⁹ Comp. 8 0 6 0.94 NG NGNG Former half of the order of 10⁹ Ex. 120 Ex. 106 16 0 0.5 0.04 G G GLatter half of the order of 10⁹ Ex. 107 16 0 5 0.42 NG G G Latter halfof the order of 10⁹ Ex. 108 8 0 0.5 C 0.08 G G G Latter half of theorder of 10¹² Ex. 109 8 0 1 0.16 G G G Former half of the order of 10⁹Ex. 110 8 0 3 0.47 G G G Former half of the order of 10⁹ Ex. 111 8 0 50.78 NG G G Former half of the order of 10⁹ Ex. 112 16 0 0.5 0.04 G G GLatter half of the order of 10⁹ Ex. 113 16 0 5 0.42 NG G G Latter halfof the order of 10⁹Silicone Adhesive Composition II-β

In Comparative Examples 121(II) to 132(II), Catalyst C was substitutedfor catalyst A in Examples 102(II) to 113(II). The results are as shownin Table 21(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 21(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 121 C 8 0 0.5 B 0.5 0.08 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 122 8 0 1 0.16 NG NG G Former halfof the order of 10⁹ Comp. Ex. 123 8 0 3 0.47 NG NG NG Former half of theorder of 10⁹ Comp. Ex. 124 8 0 5 0.78 NG NG NG Former half of the orderof 10⁹ Comp. Ex. 125 16 0 0.5 0.04 NG NG G Latter half of the order of10⁹ Comp. Ex. 126 16 0 5 0.42 NG NG NG Latter half of the order of 10⁹Comp. Ex. 127 8 0 0.5 C 0.08 NG NG G Latter half of the order of 10¹²Comp. Ex. 128 8 0 1 0.16 NG NG G Former half of the order of 10⁹ Comp.Ex. 129 8 0 3 0.47 NG NG NG Former half of the order of 10⁹ Comp. Ex.130 16 0 0.5 0.04 NG NG G Latter half of the order of 10⁹ Comp. Ex. 13116 0 1 0.08 NG NG G Latter half of the order of 10⁹ Comp. Ex. 132 16 0 30.25 NG NG NG Latter half of the order of 10⁹Silicone Adhesive Composition II-β

In Examples 114(II) to 121(II), ioninc liquid A was used in an amount of0.01 part by mass or 2 parts by mass. The results are as shown in Table22(II). The term “(II)” in the Example numbers is omitted in this Table.

TABLE 22(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Cata- part bypart by part by minute Example lyst m n mass Type mass mass 1 3 5Surface resistivity Ex. 114 A 8 0 0.5 A 0.01 0.08 G G G Latter half ofthe order of 10¹² Ex. 115 8 0 5 0.78 G G G Former half of the order of10¹² Ex. 116 16 0 0.5 0.04 G G G Latter half of the order of 10¹² Ex.117 16 0 5 0.42 G G G Latter half of the order of 10¹² Ex. 118 8 0 0.5 20.08 G G G Latter half of the order of 10¹² Ex. 119 8 0 5 0.78 G G GFormer half of the order of 10⁹ Ex. 120 16 0 0.5 0.04 G G G Latter halfof the order of 10⁹ Ex. 121 16 0 5 0.42 G G G Latter half of the orderof 10⁹Silicone Adhesive Composition II-β

In Comparative Examples 133(II) to 138(II), ioninc liquid A was used inthe amount of more than the upper limit. In Comparative Examples 139(II)to 142(II), no ionic liquid was used. The results are as shown in Table23(II). The term “(II)” in the Comparative Example numbers is omitted inthis Table.

TABLE 23(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 133 A 8 0 0.5 A 3 0.08 NG G G Latterhalf of the order of 10¹² Comp. Ex. 134 8 0 1 0.16 NG G G Former half ofthe order of 10⁹ Comp. Ex. 135 8 0 5 0.78 NG G G Former half of theorder of 10⁹ Comp. Ex. 136 16 0 0.5 0.04 NG G G Latter half of the orderof 10⁹ Comp. Ex. 137 16 0 3 0.25 NG G G Latter half of the order of 10⁹Comp. Ex. 138 16 0 5 0.42 NG G G Latter half of the order of 10⁹ Comp.Ex. 139 8 0 0.5 0 0.08 G G G Former half of the order of 10¹⁴ Comp. Ex.140 8 0 1 0.16 G G G Former half of the order of 10¹⁴ Comp. Ex. 141 8 03 0.47 G G G Former half of the order of 10¹⁴ Comp. Ex. 142 8 0 5 0.78 GG G Former half of the order of 10¹⁴Silicone Adhesive Composition II-β

In Comparative Examples 143(II) to 150(II), catalyst C was substitutedfor catalyst A in Examples 114(I) to 121(II). The results are as shownin Table 24(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 24(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 143 C 8 0 0.5 A 0.01 0.08 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 144 8 0 5 0.78 NG NG G Former halfof the order of 10¹² Comp. Ex. 145 16 0 0.5 0.04 NG NG G Latter half ofthe order of 10¹² Comp. Ex. 146 16 0 5 0.42 NG NG G Latter half of theorder of 10¹² Comp. Ex. 147 8 0 0.5 2 0.08 NG NG G Latter half of theorder of 10¹² Comp. Ex. 148 8 0 5 0.78 NG NG G Former half of the orderof 10⁹ Comp. Ex. 149 16 0 0.5 0.04 NG NG G Latter half of the order of10⁹ Comp. Ex. 150 16 0 5 0.42 NG NG G Latter half of the order of 10⁹Silicone Adhesive Composition II-β

The following Tables 25(II) to 29(II) show the cases wherepolyoxyalkylene (B-2) having two unsaturated hydrocarbon groups wasused. In Examples 122(II) to 125(II) and Comparative Examples 151(II)and 152(II), polyoxyalkylene (a) with m=8 and n=0, ioninc liquid A andcatalyst A were used in the various amounts of the polyoxyalkylene. InExamples 126(II) to 129(II) and Comparative Examples 153(II) and154(II), polyoxyalkylene (a) with m=16 and n=0, ioninc liquid A andcatalyst A were used in the various amounts of the polyoxyalkylene. Theresults are as shown in Table 25(II). The term “(II)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 25(II) Evaluation results Component (B-2) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 8 0 0.4 A 0.5 0.06 G G G Formerhalf of the order of 10¹³ Ex. 151 Ex. 122 0.5 0.07 G G G Latter half ofthe order of 10¹² Ex. 123 1 0.15 G G G Former half of the order of 10¹²Ex. 124 3 0.44 G G G Former half of the order of 10¹² Ex. 125 5 0.74 G GG Former half of the order of 10¹² Comp. 6 0.88 NG NG G Former half ofthe order of 10¹² Ex. 152 Comp. 16 0 0.4 0.03 G G G Former half of theorder of 10¹³ Ex. 153 Ex. 126 0.5 0.04 G G G Latter half of the order of10¹² Ex. 127 1 0.08 G G G Latter half of the order of 10¹² Ex. 128 30.24 G G G Latter half of the order of 10¹² Ex. 129 5 0.41 G G G Latterhalf of the order of 10¹² Comp. 6 0.49 NG NG G Latter half of the orderof 10¹² Ex. 154Silicone Adhesive Composition II-β

In Examples 130(II) to 133(II) and Comparative Examples 155(II) and156(II), polyoxyalkylene (a) with m=8 and n=0, ioninc liquid A andcatalyst A were used in the various amounts of the polyoxyalkylene. InExamples 134(II) to 137(II) and Comparative Examples 157(II) and158(II), polyoxyalkylene (a) with m=16 and n=0, ioninc liquid A andcatalyst A were used in the various amounts of the polyoxyalkylene. Theresults are as shown in Table 26(II). The term “(II)” in the Example andComparative Example numbers is omitted in this Table.

TABLE 26(II) Evaluation results Component (B-2) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 0 10 0.4 A 0.5 0.04 G G G Formerhalf of the order of 10¹³ Ex. 155 Ex. 130 0.5 0.05 G G G Latter half ofthe order of 10¹² Ex. 131 1 0.1 G G G Latter half of the order of 10¹²Ex. 132 3 0.29 G G G Latter half of the order of 10¹² Ex. 133 5 0.48 G GG Latter half of the order of 10¹² Comp. 6 0.58 NG NG G Latter half ofthe order of 10¹² Ex. 156 Comp. 12 2 0.4 0.04 G G G Former half of theorder of 10¹³ Ex. 157 Ex. 134 0.5 0.04 G G G Former half of the order of10¹² Ex. 135 1 0.09 G G G Former half of the order of 10¹² Ex. 136 30.26 G G G Former half of the order of 10¹² Ex. 137 5 0.44 G G G Formerhalf of the order of 10¹² Comp. 6 0.53 NG NG G Former half of the orderof 10¹² Ex. 158Silicone Adhesive Composition II-β

In Comparative Examples 159(II) and 172(II), ioninc liquid A andcomparative catalyst C were used together with component (B-2) shown inthe following Table in the various amounts. The results are as shown inTable 27(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 27(II) Evaluation results Component (B-2) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 159 C 8 0 0.5 A 0.5 0.07 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 160 8 0 1 A 0.5 0.15 NG NG G Formerhalf of the order of 10¹² Comp. Ex. 161 8 0 3 A 0.5 0.44 NG NG NG Formerhalf of the order of 10¹² Comp. Ex. 162 8 0 5 A 0.5 0.74 NG NG NG Formerhalf of the order of 10¹² Comp. Ex. 163 16 0 6 A 0.5 0.88 NG NG NGFormer half of the order of 10¹² Comp. Ex. 164 16 0 0.4 A 0.5 0.03 NG NGG Former half of the order of 10¹³ Comp. Ex. 165 16 0 0.5 A 0.5 0.04 NGNG G Latter half of the order of 10¹² Comp. Ex. 166 16 0 1 A 0.5 0.08 NGNG G Latter half of the order of 10¹² Comp. Ex. 167 16 0 3 A 0.5 0.24 NGNG NG Latter half of the order of 10¹² Comp. Ex. 168 0 10 5 A 0.5 0.41NG NG NG Latter half of the order of 10¹² Comp. Ex. 169 12 2 0.5 A 0.50.05 NG NG G Latter half of the order of 10¹² Comp. Ex. 170 12 2 1 A 0.50.1 NG NG G Latter half of the order of 10¹² Comp. Ex. 171 12 2 3 A 0.50.29 NG NG NG Latter half of the order of 10¹² Comp. Ex. 172 12 2 5 A0.5 0.48 NG NG NG Latter half of the order of 10¹²Silicone Adhesive Composition II-β

In Examples 138(II) to 149(II) and Comparative Examples 173(II) and174(II), ioninc liquid B or C was used. The results are as shown inTable 28(II). The term “(II)” in the Example and Comparative Examplenumbers is omitted in this Table.

TABLE 28(II) Evaluation results Component (B-2) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example Example lyst m n mass Type massmass 1 3 5 Surface resistivity Comp. A 8 0 0.4 B 0.5 0.06 G G G Formerhalf of the order of 10¹³ Ex. 173 Ex. 138 8 0 0.5 0.07 G G G Latter halfof the order of 10¹² Ex. 139 8 0 1 0.15 G G G Former half of the orderof 10¹² Ex. 140 8 0 3 0.44 G G G Former half of the order of 10¹² Ex.141 8 0 5 0.74 NG G G Former half of the order of 10¹² Comp. 8 0 6 0.88NG NG NG Former half of the order of 10¹² Ex. 174 Ex. 142 16 0 0.5 0.04G G G Latter half of the order of 10¹² Ex. 143 16 0 5 0.41 NG G G Latterhalf of the order of 10¹² Ex. 144 8 0 0.5 C 0.07 G G G Latter half ofthe order of 10¹² Ex. 145 8 0 1 0.15 G G G Former half of the order of10¹² Ex. 146 8 0 3 0.44 G G G Former half of the order of 10¹² Ex. 147 80 5 0.74 NG G G Former half of the order of 10¹² Ex. 148 16 0 0.5 0.04 GG G Latter half of the order of 10¹² Ex. 149 16 0 5 0.41 NG G G Latterhalf of the order of 10¹²Silicone Adhesive Composition II-β

In Comparative Examples 175(II) to 183(II), catalyst C was substitutedfor catalyst A in Examples 138(II) to 149(II). The results are as shownin Table 29(II). The term “(II)” in the Comparative Example numbers isomitted in this Table.

TABLE 29(II) Evaluation results Component (B-2) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 175 C 8 0 0.5 B 0.5 0.07 NG NG G Latterhalf of the order of 10¹² Comp. Ex. 176 8 0 1 0.15 NG NG G Former halfof the order of 10¹² Comp. Ex. 177 8 0 3 0.44 NG NG NG Former half ofthe order of 10¹² Comp. Ex. 178 8 0 5 0.74 NG NG NG Former half of theorder of 10¹² Comp. Ex. 179 16 0 0.5 0.04 NG NG G Latter half of theorder of 10¹² Comp. Ex. 180 16 0 5 0.41 NG NG NG Latter half of theorder of 10¹² Comp. Ex. 181 8 0 0.5 C 0.07 NG NG G Latter half of theorder of 10¹² Comp. Ex. 182 8 0 1 0.15 NG NG G Former half of the orderof 10¹² Comp. Ex. 183 8 0 3 0.44 NG NG NG Former half of the order of10¹²Silicone Adhesive Composition II-α

In Comparative Examples 184(II) to 188(II), component (B) was not used.Therefore, addition of component (c2) is unnecessary. The results are asshown in Table 30(II). The term “(II)” in the Comparative Examplenumbers is omitted in this Table.

TABLE 30(II) Evaluation results Component (B-1) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 184 A — A 0 — G G G 10¹⁵ or more Comp.Ex. 185 1 G G G 10¹⁵ or more Comp. Ex. 186 3 G G G Latter half of theorder of 10¹⁴ Comp. Ex. 187 5 G G G Latter half of the order of 10¹⁴Comp. Ex. 188 10 NG G G Latter half of the order of 10¹⁴Silicone Adhesive Composition II-α

In Examples 150(II) to 152(II), component (B-3) and catalyst A wereused. The results are as shown in Table 31(II). The term “(II)” in theExample numbers is omitted in this Table.

TABLE 31(II) Evaluation results Component (B-3) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Cata- part bypart by part by minute Example lyst m n mass Type mass mass 1 3 5Surface resistivity Ex. 150 A 2 0 1.5 A 0.5 0.75 G G G Latter half ofthe order of 10¹⁰ Ex. 151 10 0 0.40 G G G Former half of the order of10¹¹ Ex. 152 20 0 0.20 G G G Latter half of the order of 10¹¹Silicone Adhesive Composition II-α

In Comparative Examples 189(II) to 191(II), Component (B-3) and catalystC were used. The results are as shown in Table 32(II). The term “(II)”in the Comparative Example numbers is omitted in this Table.

TABLE 32(II) Evaluation results Component (B-3) Component (C) Component(c2) Curability, Amount, Amount, Amount, Heating time, Comparative Cata-part by part by part by minute Example lyst m n mass Type mass mass 1 35 Surface resistivity Comp. Ex. 189 C 2 0 1.5 A 0.5 0.75 NG NG G Latterhalf of the order of 10¹⁰ Comp. Ex. 190 C 10 0 1.5 A 0.5 0.40 NG NG GFormer half of the order of 10¹¹ Comp. Ex. 191 C 20 0 1.5 A 0.5 0.20 NGNG G Latter half of the order of 10¹¹

As shown in the Comparative Examples above, the compositions comprisingthe complex of platinum with a vinyl group-containing siloxane togetherwith the oxyalkylene having one or two unsaturated hydrocarbon groupswere inferior in the curability, Thus, they could not cure sufficientlyby heating for a short time of less than 5 minutes. In contrast, thepresent silicone adhesive compositions according to the secondembodiment cured well in a short time. Thus, they cured sufficiently byheating for less than 5 minutes, particularly for 3 minutes or less.When the adhesive tapes having the adhesive layers obtained from thepresent compositions were peeled from a tape-stuck body, no residualadhesive occurred. Further, as shown in the Examples above, the curedproducts of the present compositions comprising a combination of theoxyalkylene compound with the ionic liquid had the low surfaceresistivities of a former half of the order of 10¹⁰ to a latter half ofthe order of 10¹², i.e., 1E+10 to 9.9E+12 Ω/sq. and the excellentantistatic properties.

INDUSTRIAL APPLICABILITY

The first silicone adhesive composition of the present inventionprovides an adhesive layer which has an excellent antistatic propertyand an excellent strength of bond to various tape substrates. The secondsilicone adhesive composition of the present invention cures well byheating for a short time to provide an adhesive layer having anexcellent antistatic property. The adhesive tape having the first orsecond adhesive layer may be suitably used for masking electronic partsor in situations where generation of static electricity is undesirable.

The invention claimed is:
 1. A silicone adhesive composition, comprising(A) an addition reaction-curable silicone, (B1) a compound having atleast two unsaturated hydrocarbon groups and two (poly)oxyalkyleneresidues in one molecule, which is represented by the following formula(1):

wherein A is a tetravalent hydrocarbon group having 2 to 22 carbon atomswhich is selected from the group consisting of a linear or branched,tetravalent aliphatic saturated hydrocarbon group having 2 to 16 carbonatoms and a cyclic hydrocarbon group having 6 to 22 carbon atoms andoptionally a branched chain, R¹ is, independently of each other, ahydrogen atom, an acyl group, or a monovalent hydrocarbon group whichhas 1 to 12 carbon atoms, may have an unsaturated bond and may have anoxygen atom, two R¹s bonded to A are each aliphatic hydrocarbon groupwhich has the unsaturated bond and optionally an oxygen atom, m¹ and m²are, independently of each other, a real number of 0 to 20, n¹ and n²are, independently of each other, a real number of 0 to 10, m¹+n¹ is notzero, m²+n² is not zero, and (C₂H₄O) and (C₃H₆O) may be bonded in randomorder, and (C) an ionic liquid containing no lithium.
 2. The siliconeadhesive composition according to claim 1, wherein the compound (B1) isrepresented by the following formula (2):

wherein A and R¹ are as defined above, and m³ and m⁴ are, independentlyof each other, a real number of 1 to
 20. 3. A silicone adhesivecomposition, comprising (A) an addition reaction-curable silicone, (B1)a compound having at least two unsaturated hydrocarbon groups and two(poly)oxyalkylene residues in one molecule, which is represented by thefollowing formula (1):

wherein A is a tetravalent hydrocarbon group having 2 to 22 carbon atomswhich is selected from the group consisting of a linear or branched,tetravalent aliphatic saturated hydrocarbon group having 2 to 16 carbonatoms and a cyclic hydrocarbon group having 6 to 22 carbon atoms andoptionally a branched chain, R¹ is, independently of each other, ahydrogen atom, an acyl group, or a monovalent hydrocarbon group whichhas 1 to 12 carbon atoms, may have an unsaturated bond and may have anoxygen atom, two R¹s bonded to A are each aliphatic hydrocarbon groupwhich has the unsaturated bond and optionally an oxygen atom, m¹ and m²are, independently of each other, a real number of 0 to 20, n¹ and n²are, independently of each other, a real number of 0 to 10, m¹+n¹ is notzero, m²+n² is not zero, and (C₂H₄O) and (C₃H₆O) may be bonded in randomorder, (C) an ionic liquid containing no lithium, and (e) a platinumgroup metal catalyst which is not a complex with a compound having anunsaturated hydrocarbon bond.
 4. The silicone adhesive compositionaccording to claim 3, wherein the compound having an unsaturatedhydrocarbon bond for component (e) is an olefinic compound or a vinylgroup-containing siloxane.
 5. The silicone adhesive compositionaccording to claim 3 or 4, wherein the platinum group metal catalyst isat least one selected from the group consisting of chloroplatinic acid,a solution of chloroplatinic acid in an alcohol, and a reaction productof chloroplatinic acid with an alcohol.
 6. The silicone adhesivecomposition according to claim 3, wherein the compound (B1) isrepresented by the following formula (2):

wherein A and R¹ are as defined above, and m³ and m⁴ are, independentlyof each other, a real number of 1 to
 20. 7. The silicone adhesivecomposition according to claim 1 or 3, wherein the ionic liquid (C) isat least one selected from the group consisting of quaternary ammoniumsalts, quaternary phosphonium salts, imidazolium salts, pyridinium saltsand pyrrolidinium salts.
 8. The silicone adhesive composition accordingto claim 7, wherein the ionic liquid (C) is a quaternary ammonium saltcomposed of a quaternary ammonium cation and abis(trifluoromethylsulfonyl)imide anion.
 9. The silicone adhesivecomposition according to claim 2 or 6, wherein A in formula (1) or (2)is a linear or branched, aliphatic saturated hydrocarbon group having 2to 16 carbon atoms or a cyclic hydrocarbon group having 6 to 22 carbonatoms.
 10. The silicone adhesive composition according to claim 1 or 3,wherein an amount of component (B1) is 0.27 to 3.3 parts by mass and anamount of component (C) is 0.003 to 1.5 parts by mass, relative to 100parts by mass of the addition curable silicone (A).
 11. The siliconeadhesive composition according to claim 1, comprising, as the additioncurable silicone (A), the following components (a) to (c): (a) a lineardiorganopolysiloxane having two or more alkenyl groups in one moleculein an amount of 20 to 100 parts by mass, (b) an organopolysiloxanehaving (R⁴)₃SiO_(0.5) units and SiO₂ units in a mole ratio of the(R⁴)₃SiO_(0.5) units to the SiO₂ units of 0.6 to 1.7, wherein R⁴ is amonovalent hydrocarbon group having 1 to 10 carbon atoms, in an amountof 0 to 80 parts by mass, provided that a total amount of components (a)and (b) is 100 parts by mass, (c) an organohydrogenpolysiloxane havingtwo or more SiH groups in one molecule in an amount such that a ratio ofthe number of SiH groups in component (c) to the total number of theunsaturated hydrocarbon groups in components (a) and (B1) is 1 to 20,and further comprising: (d) a reaction inhibitor in an amount of 0 to 8parts by mass, relative to total 100 parts by mass of components (a) and(b), and (e′) a catalyst for an addition reaction in a catalytic amount,wherein the amount of component (B1) is 0.27 to 3.3 parts by mass,relative to total 100 parts by mass of components (a), (b) and (c), andthe amount of component (C) is 0.003 to 1.5 parts by mass, relative tototal 100 parts by mass of components (a), (b) and (c).
 12. The siliconeadhesive composition according to claim 3, comprising, as the additioncurable silicone (A), the following components (a) to (c): (a) a lineardiorganopolysiloxane having two or more alkenyl groups in one moleculein an amount of 20 to 100 parts by mass, (b) an organopolysiloxanehaving (R⁴)₃SiO_(0.5) units and SiO₂ units in a mole ratio of the(R⁴)₃SiO_(0.5) units to the SiO₂ units of 0.6 to 1.7, wherein R⁴ is amonovalent hydrocarbon group having 1 to 10 carbon atoms, in an amountof 0 to 80 parts by mass, provided that a total amount of components (a)and (b) is 100 parts by mass, and (c) an organohydrogenpolysiloxanehaving two or more SiH groups in one molecule in an amount such that aratio of the number of SiH groups in component (c) to the total numberof the unsaturated hydrocarbon groups in components (a) and (B1) is 1 to20, and further comprising; (d) a reaction inhibitor in an amount of 0to 8 parts by mass, relative to total 100 parts by mass of components(a) and (b), wherein the amount of component (B1) is 0.27 to 3.3 partsby mass, relative to total 100 parts by mass of components (a), (b) and(c), and the amount of component (C) is 0.003 to 1.5 parts by mass,relative to total 100 parts by mass of components (a), (b) and (c). 13.The silicone adhesive composition according to claim 1 or 3, furthercomprising an organic solvent.
 14. A cured product of the siliconeadhesive composition according to claim 1 or
 3. 15. An adhesive tapecomprising a sheet substrate at least one surface of which is laminatedwith the cured product according to claim
 14. 16. An adhesive filmcomprising a sheet substrate at least one surface of which is laminatedwith the cured product according to claim 14.